Structure

Physi-Chem Properties

Molecular Weight:  440.37
Volume:  496.961
LogP:  6.55
LogD:  4.542
LogS:  -5.345
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.458
Synthetic Accessibility Score:  5.048
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.16
MDCK Permeability:  1.546673956909217e-05
Pgp-inhibitor:  0.818
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.62
30% Bioavailability (F30%):  0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.025
Plasma Protein Binding (PPB):  93.68444061279297%
Volume Distribution (VD):  1.17
Pgp-substrate:  2.167637348175049%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.52
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.931
CYP2C9-inhibitor:  0.145
CYP2C9-substrate:  0.042
CYP2D6-inhibitor:  0.09
CYP2D6-substrate:  0.027
CYP3A4-inhibitor:  0.876
CYP3A4-substrate:  0.928

ADMET: Excretion

Clearance (CL):  9.396
Half-life (T1/2):  0.056

ADMET: Toxicity

hERG Blockers:  0.092
Human Hepatotoxicity (H-HT):  0.745
Drug-inuced Liver Injury (DILI):  0.006
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.373
Maximum Recommended Daily Dose:  0.92
Skin Sensitization:  0.941
Carcinogencity:  0.297
Eye Corrosion:  0.015
Eye Irritation:  0.02
Respiratory Toxicity:  0.985

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

  Natural Product: NPC72507

Natural Product ID:  NPC72507
Common Name*:   (3R,4Ar,6As,6Bs,8As,11R,12Ar,14Bs)-11-(Hydroxymethyl)-4,4,6A,6B,8A,11,14B-Heptamethyl-1,2,3,4A,5,7,8,9,10,12,12A,13-Dodecahydropicen-3-Ol
IUPAC Name:   (3R,4aR,6aS,6bS,8aS,11R,12aR,14bS)-11-(hydroxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4a,5,7,8,9,10,12,12a,13-dodecahydropicen-3-ol
Synonyms:  
Standard InCHIKey:  UIXJVDGAGQPTFR-ZSBHZPGCSA-N
Standard InCHI:  InChI=1S/C30H48O2/c1-25(2)22-9-8-21-20(28(22,5)12-11-24(25)32)10-13-30(7)23-18-26(3,19-31)14-15-27(23,4)16-17-29(21,30)6/h8,10,22-24,31-32H,9,11-19H2,1-7H3/t22-,23+,24+,26+,27+,28+,29+,30-/m0/s1
SMILES:  OC[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)CC=C3C(=CC[C@@H]4[C@]3(C)CC[C@H](C4(C)C)O)[C@]1(CC2)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1983444
PubChem CID:   159490
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(00)97029-8]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. stem n.a. PMID[18310955]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota seeds n.a. n.a. PMID[18603435]
NPO19870 Momordica cochinchinensis Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[19711988]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[20469887]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19870 Momordica cochinchinensis Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19870 Momordica cochinchinensis Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19870 Momordica cochinchinensis Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19870 Momordica cochinchinensis Species Cucurbitaceae 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[571159]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2098.94 nM PMID[571159]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1976.97 nM PMID[571159]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2128.14 nM PMID[571159]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1790.61 nM PMID[571159]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 1836.54 nM PMID[571159]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2065.38 nM PMID[571159]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1745.82 nM PMID[571159]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 18879.91 nM PMID[571159]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 1753.88 nM PMID[571159]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 2013.72 nM PMID[571159]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 1909.85 nM PMID[571159]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 1633.05 nM PMID[571159]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[571159]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 3228.49 nM PMID[571159]

☑ 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 NPC72507 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
0.9351 High Similarity NPC82538
0.9351 High Similarity NPC237795
0.9324 High Similarity NPC101475
0.9324 High Similarity NPC34177
0.9324 High Similarity NPC157996
0.9324 High Similarity NPC40394
0.9315 High Similarity NPC34700
0.9315 High Similarity NPC138374
0.92 High Similarity NPC196753
0.92 High Similarity NPC230295
0.92 High Similarity NPC300499
0.92 High Similarity NPC253807
0.92 High Similarity NPC98386
0.92 High Similarity NPC474989
0.92 High Similarity NPC99168
0.92 High Similarity NPC158662
0.92 High Similarity NPC22955
0.92 High Similarity NPC470396
0.9189 High Similarity NPC30590
0.9189 High Similarity NPC27765
0.9189 High Similarity NPC122418
0.9189 High Similarity NPC106432
0.9189 High Similarity NPC120098
0.9189 High Similarity NPC265328
0.9189 High Similarity NPC290598
0.9178 High Similarity NPC100334
0.9079 High Similarity NPC291379
0.9079 High Similarity NPC53744
0.9067 High Similarity NPC90979
0.9067 High Similarity NPC472805
0.8974 High Similarity NPC20853
0.8961 High Similarity NPC295131
0.8933 High Similarity NPC106364
0.8904 High Similarity NPC110799
0.8846 High Similarity NPC116202
0.8846 High Similarity NPC242350
0.8784 High Similarity NPC182717
0.8734 High Similarity NPC47763
0.8734 High Similarity NPC304285
0.8701 High Similarity NPC318136
0.8701 High Similarity NPC186191
0.8701 High Similarity NPC205455
0.8667 High Similarity NPC243342
0.8667 High Similarity NPC477138
0.8667 High Similarity NPC91858
0.8649 High Similarity NPC167706
0.8625 High Similarity NPC159168
0.8625 High Similarity NPC253402
0.8608 High Similarity NPC6707
0.8571 High Similarity NPC470758
0.8571 High Similarity NPC471798
0.8571 High Similarity NPC214570
0.8571 High Similarity NPC470711
0.8553 High Similarity NPC291503
0.8553 High Similarity NPC66566
0.8553 High Similarity NPC477923
0.8533 High Similarity NPC471799
0.8533 High Similarity NPC68443
0.8533 High Similarity NPC211009
0.8519 High Similarity NPC238992
0.85 High Similarity NPC202389
0.85 High Similarity NPC248886
0.85 High Similarity NPC201852
0.8493 Intermediate Similarity NPC32055
0.8493 Intermediate Similarity NPC216460
0.8471 Intermediate Similarity NPC301244
0.8462 Intermediate Similarity NPC275910
0.8462 Intermediate Similarity NPC6978
0.8462 Intermediate Similarity NPC138621
0.8462 Intermediate Similarity NPC167037
0.8462 Intermediate Similarity NPC244385
0.8462 Intermediate Similarity NPC285761
0.8452 Intermediate Similarity NPC161751
0.8452 Intermediate Similarity NPC95246
0.8452 Intermediate Similarity NPC474972
0.8442 Intermediate Similarity NPC202642
0.8442 Intermediate Similarity NPC73875
0.8442 Intermediate Similarity NPC189883
0.8442 Intermediate Similarity NPC46160
0.8442 Intermediate Similarity NPC237460
0.8442 Intermediate Similarity NPC470749
0.8421 Intermediate Similarity NPC471797
0.8415 Intermediate Similarity NPC133954
0.8415 Intermediate Similarity NPC191965
0.84 Intermediate Similarity NPC301226
0.84 Intermediate Similarity NPC242001
0.8395 Intermediate Similarity NPC309309
0.8395 Intermediate Similarity NPC474789
0.8395 Intermediate Similarity NPC52108
0.8395 Intermediate Similarity NPC291999
0.8378 Intermediate Similarity NPC210323
0.8354 Intermediate Similarity NPC472463
0.8354 Intermediate Similarity NPC80530
0.8354 Intermediate Similarity NPC273410
0.8354 Intermediate Similarity NPC1319
0.8333 Intermediate Similarity NPC470542
0.8333 Intermediate Similarity NPC477924
0.8333 Intermediate Similarity NPC130136
0.8333 Intermediate Similarity NPC91594
0.8313 Intermediate Similarity NPC137306
0.8313 Intermediate Similarity NPC237344
0.8313 Intermediate Similarity NPC72638
0.8313 Intermediate Similarity NPC95594
0.8313 Intermediate Similarity NPC477579
0.8313 Intermediate Similarity NPC84121
0.8313 Intermediate Similarity NPC475862
0.8313 Intermediate Similarity NPC213412
0.8313 Intermediate Similarity NPC235341
0.8313 Intermediate Similarity NPC74363
0.8312 Intermediate Similarity NPC257347
0.8312 Intermediate Similarity NPC141071
0.8312 Intermediate Similarity NPC121744
0.8312 Intermediate Similarity NPC322353
0.8312 Intermediate Similarity NPC471723
0.8312 Intermediate Similarity NPC144075
0.8312 Intermediate Similarity NPC118508
0.8293 Intermediate Similarity NPC474493
0.8293 Intermediate Similarity NPC209802
0.8293 Intermediate Similarity NPC171789
0.8293 Intermediate Similarity NPC231310
0.8293 Intermediate Similarity NPC53385
0.8289 Intermediate Similarity NPC201373
0.8276 Intermediate Similarity NPC80365
0.8267 Intermediate Similarity NPC92801
0.8267 Intermediate Similarity NPC145498
0.825 Intermediate Similarity NPC236237
0.825 Intermediate Similarity NPC236112
0.825 Intermediate Similarity NPC102253
0.825 Intermediate Similarity NPC13554
0.825 Intermediate Similarity NPC322313
0.8243 Intermediate Similarity NPC208999
0.8243 Intermediate Similarity NPC94192
0.8243 Intermediate Similarity NPC2648
0.8235 Intermediate Similarity NPC474686
0.8228 Intermediate Similarity NPC312328
0.8228 Intermediate Similarity NPC18603
0.8228 Intermediate Similarity NPC148977
0.8228 Intermediate Similarity NPC11908
0.8228 Intermediate Similarity NPC85346
0.8228 Intermediate Similarity NPC307965
0.8228 Intermediate Similarity NPC65897
0.8228 Intermediate Similarity NPC302041
0.8228 Intermediate Similarity NPC76931
0.8214 Intermediate Similarity NPC142415
0.8214 Intermediate Similarity NPC307426
0.8214 Intermediate Similarity NPC88716
0.8214 Intermediate Similarity NPC51700
0.8214 Intermediate Similarity NPC71507
0.8214 Intermediate Similarity NPC102683
0.8214 Intermediate Similarity NPC242468
0.8214 Intermediate Similarity NPC68160
0.8214 Intermediate Similarity NPC171203
0.8214 Intermediate Similarity NPC293564
0.8214 Intermediate Similarity NPC130577
0.8214 Intermediate Similarity NPC18064
0.8214 Intermediate Similarity NPC98442
0.8214 Intermediate Similarity NPC73064
0.8205 Intermediate Similarity NPC274079
0.8205 Intermediate Similarity NPC107059
0.8205 Intermediate Similarity NPC477925
0.8205 Intermediate Similarity NPC134330
0.8205 Intermediate Similarity NPC300324
0.8205 Intermediate Similarity NPC240604
0.8205 Intermediate Similarity NPC265588
0.8205 Intermediate Similarity NPC321381
0.8205 Intermediate Similarity NPC321016
0.8205 Intermediate Similarity NPC470362
0.8205 Intermediate Similarity NPC129165
0.8193 Intermediate Similarity NPC477578
0.8182 Intermediate Similarity NPC476366
0.8182 Intermediate Similarity NPC201048
0.8161 Intermediate Similarity NPC211230
0.8158 Intermediate Similarity NPC164022
0.8148 Intermediate Similarity NPC474531
0.8148 Intermediate Similarity NPC476646
0.8133 Intermediate Similarity NPC476431
0.8125 Intermediate Similarity NPC30986
0.8125 Intermediate Similarity NPC209430
0.8118 Intermediate Similarity NPC246708
0.8118 Intermediate Similarity NPC473242
0.8118 Intermediate Similarity NPC470629
0.8118 Intermediate Similarity NPC290690
0.8118 Intermediate Similarity NPC17733
0.8118 Intermediate Similarity NPC52169
0.8118 Intermediate Similarity NPC182797
0.8118 Intermediate Similarity NPC474512
0.8118 Intermediate Similarity NPC181225
0.8118 Intermediate Similarity NPC40552
0.8108 Intermediate Similarity NPC197805
0.8101 Intermediate Similarity NPC198968
0.8101 Intermediate Similarity NPC155986
0.8101 Intermediate Similarity NPC318495
0.8095 Intermediate Similarity NPC24277
0.809 Intermediate Similarity NPC88847
0.8082 Intermediate Similarity NPC163678
0.8077 Intermediate Similarity NPC240235
0.8077 Intermediate Similarity NPC162742
0.8077 Intermediate Similarity NPC231256
0.8077 Intermediate Similarity NPC104387
0.8077 Intermediate Similarity NPC178383

  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 NPC72507 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
0.9079 High Similarity NPD7645 Phase 2
0.825 Intermediate Similarity NPD7525 Registered
0.8077 Intermediate Similarity NPD7339 Approved
0.8077 Intermediate Similarity NPD6942 Approved
0.7975 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD8264 Approved
0.7841 Intermediate Similarity NPD7515 Phase 2
0.7722 Intermediate Similarity NPD6924 Approved
0.7722 Intermediate Similarity NPD6926 Approved
0.7531 Intermediate Similarity NPD6933 Approved
0.7473 Intermediate Similarity NPD7748 Approved
0.7471 Intermediate Similarity NPD3618 Phase 1
0.7468 Intermediate Similarity NPD7151 Approved
0.7468 Intermediate Similarity NPD7150 Approved
0.7468 Intermediate Similarity NPD7152 Approved
0.7442 Intermediate Similarity NPD4786 Approved
0.7436 Intermediate Similarity NPD6923 Approved
0.7436 Intermediate Similarity NPD6922 Approved
0.7416 Intermediate Similarity NPD5328 Approved
0.7412 Intermediate Similarity NPD3667 Approved
0.7381 Intermediate Similarity NPD4748 Discontinued
0.7381 Intermediate Similarity NPD7509 Discontinued
0.7342 Intermediate Similarity NPD7143 Approved
0.7342 Intermediate Similarity NPD7144 Approved
0.7262 Intermediate Similarity NPD6929 Approved
0.7253 Intermediate Similarity NPD6079 Approved
0.725 Intermediate Similarity NPD4243 Approved
0.7234 Intermediate Similarity NPD7902 Approved
0.7222 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6930 Phase 2
0.7176 Intermediate Similarity NPD6931 Approved
0.7159 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5279 Phase 3
0.7073 Intermediate Similarity NPD4785 Approved
0.7073 Intermediate Similarity NPD4784 Approved
0.7045 Intermediate Similarity NPD3666 Approved
0.7045 Intermediate Similarity NPD3133 Approved
0.7045 Intermediate Similarity NPD3665 Phase 1
0.7024 Intermediate Similarity NPD5776 Phase 2
0.7024 Intermediate Similarity NPD6932 Approved
0.7024 Intermediate Similarity NPD6925 Approved
0.7 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.6989 Remote Similarity NPD4202 Approved
0.6941 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6941 Remote Similarity NPD7145 Approved
0.6932 Remote Similarity NPD6695 Phase 3
0.6915 Remote Similarity NPD7900 Approved
0.6915 Remote Similarity NPD7901 Clinical (unspecified phase)
0.686 Remote Similarity NPD6683 Phase 2
0.6854 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6804 Remote Similarity NPD7638 Approved
0.679 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6786 Remote Similarity NPD5275 Approved
0.6786 Remote Similarity NPD4190 Phase 3
0.6782 Remote Similarity NPD7332 Phase 2
0.6782 Remote Similarity NPD7514 Phase 3
0.6778 Remote Similarity NPD6893 Approved
0.6771 Remote Similarity NPD4697 Phase 3
0.6771 Remote Similarity NPD5221 Approved
0.6771 Remote Similarity NPD5222 Approved
0.6771 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6735 Remote Similarity NPD7640 Approved
0.6735 Remote Similarity NPD7639 Approved
0.6705 Remote Similarity NPD6902 Approved
0.6705 Remote Similarity NPD6898 Phase 1
0.6702 Remote Similarity NPD6411 Approved
0.6701 Remote Similarity NPD4755 Approved
0.6701 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD4195 Approved
0.6667 Remote Similarity NPD3668 Phase 3
0.6633 Remote Similarity NPD5290 Discontinued
0.6632 Remote Similarity NPD6399 Phase 3
0.663 Remote Similarity NPD7750 Discontinued
0.663 Remote Similarity NPD7524 Approved
0.6591 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5286 Approved
0.6566 Remote Similarity NPD4696 Approved
0.6566 Remote Similarity NPD4700 Approved
0.6566 Remote Similarity NPD5285 Approved
0.6559 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6538 Remote Similarity NPD368 Approved
0.6526 Remote Similarity NPD8034 Phase 2
0.6526 Remote Similarity NPD8035 Phase 2
0.6522 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4694 Approved
0.6522 Remote Similarity NPD5280 Approved
0.6506 Remote Similarity NPD4787 Phase 1
0.65 Remote Similarity NPD5223 Approved
0.6489 Remote Similarity NPD6101 Approved
0.6489 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6489 Remote Similarity NPD4753 Phase 2
0.6444 Remote Similarity NPD4223 Phase 3
0.6444 Remote Similarity NPD4221 Approved
0.6436 Remote Similarity NPD5226 Approved
0.6436 Remote Similarity NPD5211 Phase 2
0.6436 Remote Similarity NPD4633 Approved
0.6436 Remote Similarity NPD5225 Approved
0.6436 Remote Similarity NPD5224 Approved
0.6429 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7614 Phase 1
0.6429 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6413 Remote Similarity NPD5329 Approved
0.6408 Remote Similarity NPD6402 Approved
0.6408 Remote Similarity NPD7128 Approved
0.6408 Remote Similarity NPD5739 Approved
0.6408 Remote Similarity NPD6675 Approved
0.6404 Remote Similarity NPD4695 Discontinued
0.6386 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6386 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6381 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4788 Approved
0.6373 Remote Similarity NPD5175 Approved
0.6373 Remote Similarity NPD4754 Approved
0.6373 Remote Similarity NPD5174 Approved
0.6364 Remote Similarity NPD3617 Approved
0.6354 Remote Similarity NPD7087 Discontinued
0.6344 Remote Similarity NPD7334 Approved
0.6344 Remote Similarity NPD7146 Approved
0.6344 Remote Similarity NPD5330 Approved
0.6344 Remote Similarity NPD6684 Approved
0.6344 Remote Similarity NPD7521 Approved
0.6344 Remote Similarity NPD6409 Approved
0.6322 Remote Similarity NPD6117 Approved
0.6311 Remote Similarity NPD5141 Approved
0.6304 Remote Similarity NPD4197 Approved
0.6286 Remote Similarity NPD7320 Approved
0.6286 Remote Similarity NPD6899 Approved
0.6286 Remote Similarity NPD6881 Approved
0.6279 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6277 Remote Similarity NPD3573 Approved
0.6275 Remote Similarity NPD7632 Discontinued
0.625 Remote Similarity NPD4767 Approved
0.625 Remote Similarity NPD6116 Phase 1
0.625 Remote Similarity NPD4768 Approved
0.6237 Remote Similarity NPD1696 Phase 3
0.6226 Remote Similarity NPD6372 Approved
0.6226 Remote Similarity NPD6373 Approved
0.6211 Remote Similarity NPD6903 Approved
0.6207 Remote Similarity NPD3703 Phase 2
0.62 Remote Similarity NPD6083 Phase 2
0.62 Remote Similarity NPD6084 Phase 2
0.619 Remote Similarity NPD5697 Approved
0.619 Remote Similarity NPD5701 Approved
0.6186 Remote Similarity NPD5281 Approved
0.6186 Remote Similarity NPD5284 Approved
0.6184 Remote Similarity NPD342 Phase 1
0.618 Remote Similarity NPD6697 Approved
0.618 Remote Similarity NPD6114 Approved
0.618 Remote Similarity NPD6118 Approved
0.618 Remote Similarity NPD6115 Approved
0.6176 Remote Similarity NPD4159 Approved
0.617 Remote Similarity NPD4688 Approved
0.617 Remote Similarity NPD5690 Phase 2
0.617 Remote Similarity NPD4690 Approved
0.617 Remote Similarity NPD4693 Phase 3
0.617 Remote Similarity NPD4689 Approved
0.617 Remote Similarity NPD4138 Approved
0.617 Remote Similarity NPD4519 Discontinued
0.617 Remote Similarity NPD4623 Approved
0.617 Remote Similarity NPD5205 Approved
0.6168 Remote Similarity NPD7290 Approved
0.6168 Remote Similarity NPD7102 Approved
0.6168 Remote Similarity NPD6883 Approved
0.6162 Remote Similarity NPD5210 Approved
0.6162 Remote Similarity NPD4629 Approved
0.6154 Remote Similarity NPD4692 Approved
0.6154 Remote Similarity NPD4139 Approved
0.6146 Remote Similarity NPD6051 Approved
0.6139 Remote Similarity NPD4225 Approved
0.6132 Remote Similarity NPD6011 Approved
0.6132 Remote Similarity NPD4729 Approved
0.6132 Remote Similarity NPD5128 Approved
0.6132 Remote Similarity NPD5168 Approved
0.6132 Remote Similarity NPD4730 Approved
0.6122 Remote Similarity NPD5133 Approved
0.6122 Remote Similarity NPD5778 Approved
0.6122 Remote Similarity NPD5779 Approved
0.6118 Remote Similarity NPD4245 Approved
0.6118 Remote Similarity NPD4244 Approved
0.6111 Remote Similarity NPD6847 Approved
0.6111 Remote Similarity NPD8130 Phase 1
0.6111 Remote Similarity NPD6649 Approved
0.6111 Remote Similarity NPD6869 Approved
0.6111 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6617 Approved
0.6111 Remote Similarity NPD6650 Approved
0.6104 Remote Similarity NPD4219 Approved
0.61 Remote Similarity NPD7732 Phase 3
0.6092 Remote Similarity NPD5733 Approved
0.6082 Remote Similarity NPD7136 Phase 2
0.6082 Remote Similarity NPD4096 Approved
0.6075 Remote Similarity NPD6013 Approved
0.6075 Remote Similarity NPD6014 Approved
0.6075 Remote Similarity NPD6012 Approved
0.6055 Remote Similarity NPD8297 Approved
0.6055 Remote Similarity NPD6882 Approved
0.6053 Remote Similarity NPD7503 Approved
0.6044 Remote Similarity NPD6928 Phase 2
0.6042 Remote Similarity NPD6672 Approved
0.6042 Remote Similarity NPD4722 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