Structure

Physi-Chem Properties

Molecular Weight:  248.09
Volume:  260.758
LogP:  3.148
LogD:  2.93
LogS:  -4.915
# Rotatable Bonds:  0
TPSA:  37.79
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.51
Synthetic Accessibility Score:  2.202
Fsp3:  0.062
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.894
MDCK Permeability:  2.0597211914719082e-05
Pgp-inhibitor:  0.027
Pgp-substrate:  0.044
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.738
30% Bioavailability (F30%):  0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.858
Plasma Protein Binding (PPB):  95.43671417236328%
Volume Distribution (VD):  0.628
Pgp-substrate:  1.4828168153762817%

ADMET: Metabolism

CYP1A2-inhibitor:  0.987
CYP1A2-substrate:  0.849
CYP2C19-inhibitor:  0.742
CYP2C19-substrate:  0.327
CYP2C9-inhibitor:  0.514
CYP2C9-substrate:  0.874
CYP2D6-inhibitor:  0.741
CYP2D6-substrate:  0.754
CYP3A4-inhibitor:  0.556
CYP3A4-substrate:  0.34

ADMET: Excretion

Clearance (CL):  3.752
Half-life (T1/2):  0.188

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.12
Drug-inuced Liver Injury (DILI):  0.575
AMES Toxicity:  0.902
Rat Oral Acute Toxicity:  0.26
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.834
Carcinogencity:  0.906
Eye Corrosion:  0.018
Eye Irritation:  0.981
Respiratory Toxicity:  0.95

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC184437

Natural Product ID:  NPC184437
Common Name*:   Hydroxycryptolepine
IUPAC Name:   n.a.
Synonyms:   Hydroxycryptolepine
Standard InCHIKey:  GOTUAZGWJVYHRE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12N2O/c1-18-13-9-5-3-7-11(13)16(19)14-15(18)10-6-2-4-8-12(10)17-14/h2-9,19H,1H3
SMILES:  Cn1c2ccccc2c(c2c1c1ccccc1n2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504189
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000061] Indoloquinolines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. n.a. n.a. PMID[14640526]
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. depth of 25 m off the shore of Keomun Island, Korea 2004-AUG PMID[18407691]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO20912 Wisteria brachybotrys Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[2853205]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32998509]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[9249972]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[9667966]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21890 Epidendrum moseni Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20169 Alseodaphne perakensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20989 Calea integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20912 Wisteria brachybotrys Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17131 Yucca periculosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20299 Strongylophora durissima n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18755 Fumaria judaica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 48194.78 nM PMID[513165]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 48640.72 nM PMID[513165]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 50466.13 nM PMID[513165]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 3459.39 nM PMID[513165]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 41209.75 nM PMID[513165]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 27669.42 nM PMID[513165]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 37670.38 nM PMID[513165]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 85901.35 nM PMID[513165]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 84722.74 nM PMID[513165]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 45708.82 nM PMID[513165]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 54075.43 nM PMID[513165]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 34119.29 nM PMID[513165]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 53333.49 nM PMID[513165]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 734.51 nM PMID[513165]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 49431.07 nM PMID[513165]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 59156.16 nM PMID[513165]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 8912.51 nM PMID[513165]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 35399.73 nM PMID[513165]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 90573.26 nM PMID[513165]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 6516.28 nM PMID[513165]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[513165]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 83176.38 nM PMID[513165]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.031 ug.mL-1 PMID[513164]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.059 ug.mL-1 PMID[513164]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.045 ug.mL-1 PMID[513164]
NPT474 Organism Plasmodium berghei Plasmodium berghei Activity = 43.2 % PMID[513164]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.027 ug.mL-1 PMID[513166]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.027 ug.mL-1 PMID[513166]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC184437 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.84 Intermediate Similarity NPC296163
0.8209 Intermediate Similarity NPC476950
0.814 Intermediate Similarity NPC192209
0.8102 Intermediate Similarity NPC476687
0.8102 Intermediate Similarity NPC476685
0.8102 Intermediate Similarity NPC476689
0.8079 Intermediate Similarity NPC476231
0.7829 Intermediate Similarity NPC187036
0.7826 Intermediate Similarity NPC226662
0.7786 Intermediate Similarity NPC147957
0.7682 Intermediate Similarity NPC471132
0.7584 Intermediate Similarity NPC254798
0.7576 Intermediate Similarity NPC288232
0.7548 Intermediate Similarity NPC27904
0.7516 Intermediate Similarity NPC471130
0.75 Intermediate Similarity NPC37584
0.75 Intermediate Similarity NPC88970
0.7483 Intermediate Similarity NPC288445
0.7452 Intermediate Similarity NPC476118
0.7447 Intermediate Similarity NPC9856
0.7376 Intermediate Similarity NPC259098
0.7376 Intermediate Similarity NPC197680
0.7357 Intermediate Similarity NPC250476
0.7333 Intermediate Similarity NPC313449
0.7323 Intermediate Similarity NPC178681
0.7278 Intermediate Similarity NPC191863
0.7278 Intermediate Similarity NPC289776
0.7278 Intermediate Similarity NPC133470
0.7273 Intermediate Similarity NPC231382
0.7219 Intermediate Similarity NPC470824
0.7163 Intermediate Similarity NPC325013
0.7134 Intermediate Similarity NPC141353
0.7113 Intermediate Similarity NPC476249
0.7086 Intermediate Similarity NPC60553
0.7078 Intermediate Similarity NPC300596
0.7078 Intermediate Similarity NPC237649
0.7067 Intermediate Similarity NPC471574
0.7032 Intermediate Similarity NPC144691
0.7025 Intermediate Similarity NPC477889
0.6988 Remote Similarity NPC471743
0.6985 Remote Similarity NPC205652
0.6985 Remote Similarity NPC470550
0.6946 Remote Similarity NPC326575
0.6928 Remote Similarity NPC477890
0.6928 Remote Similarity NPC136002
0.6909 Remote Similarity NPC158129
0.6905 Remote Similarity NPC72980
0.6901 Remote Similarity NPC283130
0.6901 Remote Similarity NPC328683
0.6897 Remote Similarity NPC92803
0.6894 Remote Similarity NPC131718
0.6887 Remote Similarity NPC243162
0.6879 Remote Similarity NPC18890
0.6875 Remote Similarity NPC26850
0.6867 Remote Similarity NPC166667
0.6863 Remote Similarity NPC308197
0.6852 Remote Similarity NPC471177
0.6852 Remote Similarity NPC59779
0.6852 Remote Similarity NPC124542
0.6829 Remote Similarity NPC278887
0.6826 Remote Similarity NPC475594
0.6824 Remote Similarity NPC477891
0.6797 Remote Similarity NPC33168
0.6791 Remote Similarity NPC302790
0.6786 Remote Similarity NPC203754
0.6786 Remote Similarity NPC150048
0.6786 Remote Similarity NPC475607
0.6776 Remote Similarity NPC472243
0.6768 Remote Similarity NPC471178
0.6766 Remote Similarity NPC471294
0.6766 Remote Similarity NPC34508
0.6765 Remote Similarity NPC39822
0.676 Remote Similarity NPC212213
0.6757 Remote Similarity NPC53044
0.6747 Remote Similarity NPC477888
0.6746 Remote Similarity NPC474081
0.6744 Remote Similarity NPC203635
0.6744 Remote Similarity NPC472294
0.6743 Remote Similarity NPC471195
0.6743 Remote Similarity NPC471196
0.6731 Remote Similarity NPC472100
0.673 Remote Similarity NPC184161
0.672 Remote Similarity NPC78154
0.6718 Remote Similarity NPC291610
0.6712 Remote Similarity NPC478079
0.6709 Remote Similarity NPC37548
0.6708 Remote Similarity NPC315257
0.6707 Remote Similarity NPC189116
0.6707 Remote Similarity NPC102423
0.6689 Remote Similarity NPC325599
0.6688 Remote Similarity NPC161292
0.6687 Remote Similarity NPC278874
0.6687 Remote Similarity NPC44161
0.6687 Remote Similarity NPC26872
0.6687 Remote Similarity NPC317430
0.6686 Remote Similarity NPC243058
0.6686 Remote Similarity NPC134586
0.6686 Remote Similarity NPC288943
0.6667 Remote Similarity NPC324149
0.6667 Remote Similarity NPC475685
0.6667 Remote Similarity NPC474409
0.6667 Remote Similarity NPC208060
0.6667 Remote Similarity NPC264580
0.6667 Remote Similarity NPC242556
0.6667 Remote Similarity NPC314141
0.6667 Remote Similarity NPC164802
0.6667 Remote Similarity NPC314573
0.6667 Remote Similarity NPC253476
0.6647 Remote Similarity NPC211997
0.6647 Remote Similarity NPC219848
0.6647 Remote Similarity NPC470003
0.6647 Remote Similarity NPC471742
0.6646 Remote Similarity NPC85651
0.6646 Remote Similarity NPC242000
0.6643 Remote Similarity NPC257490
0.6643 Remote Similarity NPC82963
0.6627 Remote Similarity NPC472115
0.6627 Remote Similarity NPC472114
0.6626 Remote Similarity NPC471122
0.6625 Remote Similarity NPC117032
0.6623 Remote Similarity NPC300299
0.6618 Remote Similarity NPC470127
0.6609 Remote Similarity NPC476319
0.6608 Remote Similarity NPC256268
0.6608 Remote Similarity NPC475761
0.6608 Remote Similarity NPC270009
0.6608 Remote Similarity NPC474041
0.6607 Remote Similarity NPC476688
0.6607 Remote Similarity NPC105758
0.6607 Remote Similarity NPC476686
0.6606 Remote Similarity NPC159319
0.6605 Remote Similarity NPC285469
0.6605 Remote Similarity NPC477157
0.6605 Remote Similarity NPC10875
0.6605 Remote Similarity NPC10730
0.6605 Remote Similarity NPC477156
0.6604 Remote Similarity NPC187951
0.6603 Remote Similarity NPC472103
0.6603 Remote Similarity NPC473804
0.6596 Remote Similarity NPC311737
0.6596 Remote Similarity NPC38458
0.6593 Remote Similarity NPC249040
0.659 Remote Similarity NPC471785
0.659 Remote Similarity NPC48938
0.6588 Remote Similarity NPC24594
0.6588 Remote Similarity NPC472122
0.6585 Remote Similarity NPC320064
0.6581 Remote Similarity NPC472241
0.6581 Remote Similarity NPC238499
0.6577 Remote Similarity NPC314098
0.6575 Remote Similarity NPC239954
0.6571 Remote Similarity NPC90415
0.6568 Remote Similarity NPC259545
0.6568 Remote Similarity NPC313791
0.6568 Remote Similarity NPC472123
0.6567 Remote Similarity NPC211551
0.6564 Remote Similarity NPC469428
0.6564 Remote Similarity NPC129721
0.6561 Remote Similarity NPC119569
0.6561 Remote Similarity NPC116519
0.6557 Remote Similarity NPC471944
0.6556 Remote Similarity NPC472193
0.6554 Remote Similarity NPC150863
0.6554 Remote Similarity NPC212125
0.6552 Remote Similarity NPC190007
0.655 Remote Similarity NPC293472
0.655 Remote Similarity NPC283152
0.6548 Remote Similarity NPC164664
0.6548 Remote Similarity NPC473764
0.6548 Remote Similarity NPC314940
0.6545 Remote Similarity NPC47298
0.6545 Remote Similarity NPC224632
0.6545 Remote Similarity NPC315214
0.6545 Remote Similarity NPC177404
0.6543 Remote Similarity NPC470507
0.6543 Remote Similarity NPC471458
0.6543 Remote Similarity NPC38736
0.6536 Remote Similarity NPC198673
0.6536 Remote Similarity NPC126637
0.6532 Remote Similarity NPC192270
0.6532 Remote Similarity NPC314394
0.6532 Remote Similarity NPC144114
0.6529 Remote Similarity NPC329688
0.6529 Remote Similarity NPC189812
0.6529 Remote Similarity NPC469938
0.6527 Remote Similarity NPC98187
0.6524 Remote Similarity NPC84508
0.6524 Remote Similarity NPC103250
0.6524 Remote Similarity NPC291359
0.6522 Remote Similarity NPC153769
0.6516 Remote Similarity NPC314113
0.6516 Remote Similarity NPC280853
0.6514 Remote Similarity NPC94943
0.6512 Remote Similarity NPC88363
0.6512 Remote Similarity NPC133261
0.6512 Remote Similarity NPC472443
0.6506 Remote Similarity NPC204867
0.6506 Remote Similarity NPC469541
0.6506 Remote Similarity NPC32028
0.65 Remote Similarity NPC124005

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC184437 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8169 Intermediate Similarity NPD6301 Phase 2
0.8112 Intermediate Similarity NPD6506 Clinical (unspecified phase)
0.8058 Intermediate Similarity NPD2791 Discontinued
0.7973 Intermediate Similarity NPD2882 Phase 1
0.7692 Intermediate Similarity NPD3864 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD4430 Phase 2
0.7664 Intermediate Similarity NPD6320 Approved
0.7612 Intermediate Similarity NPD2210 Approved
0.7612 Intermediate Similarity NPD2212 Approved
0.76 Intermediate Similarity NPD5546 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD5599 Discontinued
0.7532 Intermediate Similarity NPD7735 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5631 Phase 3
0.75 Intermediate Similarity NPD5663 Discontinued
0.75 Intermediate Similarity NPD995 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD2468 Approved
0.7468 Intermediate Similarity NPD2469 Approved
0.7452 Intermediate Similarity NPD5140 Approved
0.7452 Intermediate Similarity NPD5138 Approved
0.7391 Intermediate Similarity NPD5078 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD4871 Phase 2
0.7386 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6158 Phase 2
0.7365 Intermediate Similarity NPD1908 Phase 2
0.7355 Intermediate Similarity NPD2789 Approved
0.7333 Intermediate Similarity NPD7480 Approved
0.7333 Intermediate Similarity NPD7481 Approved
0.7325 Intermediate Similarity NPD6524 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD3277 Phase 3
0.7315 Intermediate Similarity NPD1592 Phase 3
0.7303 Intermediate Similarity NPD5881 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD1595 Approved
0.7292 Intermediate Similarity NPD1594 Phase 3
0.7261 Intermediate Similarity NPD6060 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD5595 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD6707 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD1001 Discontinued
0.7114 Intermediate Similarity NPD6522 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD2840 Approved
0.7099 Intermediate Similarity NPD6300 Approved
0.7099 Intermediate Similarity NPD6299 Approved
0.7081 Intermediate Similarity NPD3363 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3278 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2622 Approved
0.7044 Intermediate Similarity NPD4485 Approved
0.7044 Intermediate Similarity NPD5255 Approved
0.7042 Intermediate Similarity NPD4985 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3148 Approved
0.7037 Intermediate Similarity NPD3149 Approved
0.7037 Intermediate Similarity NPD2659 Approved
0.7037 Intermediate Similarity NPD2658 Approved
0.7037 Intermediate Similarity NPD3147 Approved
0.7037 Intermediate Similarity NPD3150 Approved
0.703 Intermediate Similarity NPD6492 Phase 2
0.703 Intermediate Similarity NPD5153 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD3883 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD1106 Discontinued
0.6993 Remote Similarity NPD3813 Approved
0.6986 Remote Similarity NPD2322 Discovery
0.698 Remote Similarity NPD4411 Phase 1
0.698 Remote Similarity NPD4410 Clinical (unspecified phase)
0.697 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4019 Clinical (unspecified phase)
0.6963 Remote Similarity NPD1762 Approved
0.6963 Remote Similarity NPD1764 Approved
0.6959 Remote Similarity NPD2470 Clinical (unspecified phase)
0.6948 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6928 Remote Similarity NPD5065 Approved
0.6923 Remote Similarity NPD7867 Phase 1
0.6917 Remote Similarity NPD2679 Approved
0.6917 Remote Similarity NPD2678 Approved
0.6906 Remote Similarity NPD5657 Phase 3
0.6901 Remote Similarity NPD478 Approved
0.6894 Remote Similarity NPD993 Approved
0.6894 Remote Similarity NPD990 Approved
0.6884 Remote Similarity NPD2464 Approved
0.6884 Remote Similarity NPD2463 Approved
0.6884 Remote Similarity NPD2467 Approved
0.6882 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5596 Phase 2
0.6879 Remote Similarity NPD2328 Phase 2
0.6879 Remote Similarity NPD3329 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6848 Remote Similarity NPD1326 Approved
0.6848 Remote Similarity NPD1325 Approved
0.6845 Remote Similarity NPD6159 Phase 2
0.6842 Remote Similarity NPD5923 Phase 1
0.6824 Remote Similarity NPD4203 Approved
0.6824 Remote Similarity NPD1316 Discontinued
0.6824 Remote Similarity NPD4204 Approved
0.6821 Remote Similarity NPD6141 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2387 Approved
0.6818 Remote Similarity NPD3525 Discontinued
0.6815 Remote Similarity NPD9376 Approved
0.6806 Remote Similarity NPD1937 Approved
0.6802 Remote Similarity NPD6344 Clinical (unspecified phase)
0.679 Remote Similarity NPD5989 Phase 1
0.6783 Remote Similarity NPD964 Approved
0.6782 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6779 Remote Similarity NPD7200 Approved
0.6776 Remote Similarity NPD1884 Approved
0.6774 Remote Similarity NPD6017 Discontinued
0.677 Remote Similarity NPD1861 Discovery
0.6766 Remote Similarity NPD1226 Approved
0.6765 Remote Similarity NPD6452 Discontinued
0.6763 Remote Similarity NPD6070 Approved
0.6763 Remote Similarity NPD6069 Approved
0.6752 Remote Similarity NPD4703 Approved
0.6752 Remote Similarity NPD4702 Approved
0.6743 Remote Similarity NPD3321 Discontinued
0.6741 Remote Similarity NPD1108 Approved
0.6741 Remote Similarity NPD1107 Approved
0.6732 Remote Similarity NPD6789 Approved
0.6731 Remote Similarity NPD5414 Phase 2
0.673 Remote Similarity NPD9715 Phase 2
0.6728 Remote Similarity NPD1554 Clinical (unspecified phase)
0.6727 Remote Similarity NPD1965 Approved
0.6727 Remote Similarity NPD3587 Clinical (unspecified phase)
0.6723 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6722 Remote Similarity NPD5547 Clinical (unspecified phase)
0.6714 Remote Similarity NPD313 Approved
0.6707 Remote Similarity NPD3789 Approved
0.6707 Remote Similarity NPD3776 Discontinued
0.6707 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4083 Discontinued
0.6705 Remote Similarity NPD6227 Discontinued
0.6689 Remote Similarity NPD1883 Approved
0.6688 Remote Similarity NPD7469 Discontinued
0.6686 Remote Similarity NPD2380 Approved
0.6686 Remote Similarity NPD2381 Approved
0.6686 Remote Similarity NPD2382 Approved
0.6667 Remote Similarity NPD2913 Approved
0.6667 Remote Similarity NPD6878 Phase 2
0.6667 Remote Similarity NPD2244 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4895 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6879 Phase 2
0.6667 Remote Similarity NPD6606 Clinical (unspecified phase)
0.6667 Remote Similarity NPD477 Phase 1
0.6667 Remote Similarity NPD2914 Approved
0.6648 Remote Similarity NPD5117 Phase 2
0.6647 Remote Similarity NPD3503 Approved
0.6647 Remote Similarity NPD3504 Approved
0.6646 Remote Similarity NPD1397 Clinical (unspecified phase)
0.6646 Remote Similarity NPD3487 Phase 1
0.6646 Remote Similarity NPD6285 Phase 2
0.6646 Remote Similarity NPD4432 Discontinued
0.6642 Remote Similarity NPD3546 Approved
0.6642 Remote Similarity NPD3545 Approved
0.6629 Remote Similarity NPD4951 Discontinued
0.6629 Remote Similarity NPD2383 Phase 1
0.6629 Remote Similarity NPD3403 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6767 Clinical (unspecified phase)
0.6625 Remote Similarity NPD3248 Phase 1
0.6624 Remote Similarity NPD4351 Clinical (unspecified phase)
0.6624 Remote Similarity NPD5839 Clinical (unspecified phase)
0.6618 Remote Similarity NPD1539 Approved
0.6618 Remote Similarity NPD4116 Approved
0.6609 Remote Similarity NPD6557 Phase 2
0.6607 Remote Similarity NPD4150 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6607 Remote Similarity NPD3975 Discontinued
0.6607 Remote Similarity NPD3824 Phase 1
0.6605 Remote Similarity NPD6396 Clinical (unspecified phase)
0.6605 Remote Similarity NPD6395 Phase 2
0.6605 Remote Similarity NPD2326 Approved
0.6593 Remote Similarity NPD4115 Approved
0.6593 Remote Similarity NPD4114 Approved
0.6591 Remote Similarity NPD1417 Approved
0.6591 Remote Similarity NPD4334 Discontinued
0.6591 Remote Similarity NPD1419 Approved
0.6587 Remote Similarity NPD4640 Approved
0.6587 Remote Similarity NPD4639 Approved
0.6587 Remote Similarity NPD4638 Approved
0.6581 Remote Similarity NPD1649 Discontinued
0.6577 Remote Similarity NPD4300 Clinical (unspecified phase)
0.6577 Remote Similarity NPD4275 Approved
0.6577 Remote Similarity NPD4274 Approved
0.6577 Remote Similarity NPD3720 Discontinued
0.6573 Remote Similarity NPD7570 Approved
0.6573 Remote Similarity NPD2340 Discontinued
0.6573 Remote Similarity NPD5587 Approved
0.6573 Remote Similarity NPD7569 Approved
0.6569 Remote Similarity NPD4253 Approved
0.6569 Remote Similarity NPD4254 Approved
0.6568 Remote Similarity NPD3224 Phase 2
0.6564 Remote Similarity NPD2582 Approved
0.6564 Remote Similarity NPD2581 Approved
0.6562 Remote Similarity NPD6575 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4462 Approved
0.6562 Remote Similarity NPD4463 Approved
0.6558 Remote Similarity NPD1864 Clinical (unspecified phase)
0.6558 Remote Similarity NPD1866 Approved
0.6558 Remote Similarity NPD1870 Approved
0.6557 Remote Similarity NPD4511 Phase 1
0.6554 Remote Similarity NPD3439 Approved
0.6554 Remote Similarity NPD9284 Approved
0.6552 Remote Similarity NPD7461 Approved
0.655 Remote Similarity NPD5670 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data