Structure

Physi-Chem Properties

Molecular Weight:  518.25
Volume:  510.331
LogP:  -1.08
LogD:  -0.354
LogS:  -2.613
# Rotatable Bonds:  3
TPSA:  198.32
# H-Bond Aceptor:  13
# H-Bond Donor:  7
# Rings:  2
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.257
Synthetic Accessibility Score:  4.787
Fsp3:  0.5
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -7.016
MDCK Permeability:  1.5479413377761375e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.978
Human Intestinal Absorption (HIA):  0.434
20% Bioavailability (F20%):  0.713
30% Bioavailability (F30%):  0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.21
Plasma Protein Binding (PPB):  15.196731567382812%
Volume Distribution (VD):  0.286
Pgp-substrate:  73.697021484375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.018
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.066
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.091
CYP3A4-inhibitor:  0.02
CYP3A4-substrate:  0.02

ADMET: Excretion

Clearance (CL):  1.797
Half-life (T1/2):  0.772

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.762
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.084
Maximum Recommended Daily Dose:  0.005
Skin Sensitization:  0.04
Carcinogencity:  0.002
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.039

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

  Natural Product: NPC317254

Natural Product ID:  NPC317254
Common Name*:   3-[(4-Hydroxyphenyl)Methyl]-9,12-Dimethyl-6-Propan-2-Yl-1,4,7,10,13,16-Hexazacyclooctadecane-2,5,8,11,14,17-Hexone
IUPAC Name:   3-[(4-hydroxyphenyl)methyl]-9,12-dimethyl-6-propan-2-yl-1,4,7,10,13,16-hexazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:  
Standard InCHIKey:  XMBYOZQFNHPCMB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H34N6O7/c1-12(2)20-24(37)29-17(9-15-5-7-16(31)8-6-15)23(36)26-10-18(32)25-11-19(33)27-13(3)21(34)28-14(4)22(35)30-20/h5-8,12-14,17,20,31H,9-11H2,1-4H3,(H,25,32)(H,26,36)(H,27,33)(H,28,34)(H,29,37)(H,30,35)
SMILES:  OC1=NCC(=NC(C)C(=NC(C(=NC(C(=NC(C(=NC1)O)Cc1ccc(cc1)O)O)C(C)C)O)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2002400
PubChem CID:   362685
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000348] Peptides
            • [CHEMONTID:0004831] Oligopeptides

*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
NPO11597 Stellaria dichotoma Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[15387643]
NPO11597 Stellaria dichotoma Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[16309326]
NPO11597 Stellaria dichotoma Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11597.2 Stellaria dichotoma l. var. lanceolata bge. Varieties Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11597 Stellaria dichotoma Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11597 Stellaria dichotoma Species Caryophyllaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 50815.94 nM PMID[572727]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 10715.19 nM PMID[572727]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 100000.0 nM PMID[572727]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 100000.0 nM PMID[572727]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572727]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 30130.06 nM PMID[572727]

☑ 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 NPC317254 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
0.964 High Similarity NPC283760
0.9364 High Similarity NPC118202
0.9352 High Similarity NPC474149
0.9259 High Similarity NPC258056
0.9159 High Similarity NPC231705
0.9115 High Similarity NPC311737
0.9115 High Similarity NPC38458
0.9074 High Similarity NPC142297
0.9027 High Similarity NPC82963
0.8879 High Similarity NPC178902
0.8729 High Similarity NPC474862
0.8699 High Similarity NPC326966
0.8649 High Similarity NPC24101
0.8649 High Similarity NPC96224
0.8482 Intermediate Similarity NPC153690
0.8475 Intermediate Similarity NPC319950
0.8455 Intermediate Similarity NPC296712
0.8425 Intermediate Similarity NPC6570
0.8387 Intermediate Similarity NPC478147
0.8333 Intermediate Similarity NPC244866
0.8319 Intermediate Similarity NPC268572
0.8318 Intermediate Similarity NPC25565
0.8281 Intermediate Similarity NPC64205
0.8268 Intermediate Similarity NPC267237
0.8264 Intermediate Similarity NPC27581
0.8241 Intermediate Similarity NPC475439
0.8241 Intermediate Similarity NPC473501
0.824 Intermediate Similarity NPC325651
0.8231 Intermediate Similarity NPC197921
0.8231 Intermediate Similarity NPC476989
0.8205 Intermediate Similarity NPC142599
0.8182 Intermediate Similarity NPC155847
0.8182 Intermediate Similarity NPC289381
0.8168 Intermediate Similarity NPC91953
0.8168 Intermediate Similarity NPC168861
0.8168 Intermediate Similarity NPC469360
0.8165 Intermediate Similarity NPC107619
0.8115 Intermediate Similarity NPC142577
0.8083 Intermediate Similarity NPC122009
0.8017 Intermediate Similarity NPC43275
0.8015 Intermediate Similarity NPC214988
0.8 Intermediate Similarity NPC283468
0.7965 Intermediate Similarity NPC113326
0.7965 Intermediate Similarity NPC194390
0.7965 Intermediate Similarity NPC224610
0.7965 Intermediate Similarity NPC88267
0.7949 Intermediate Similarity NPC166837
0.7944 Intermediate Similarity NPC55561
0.7937 Intermediate Similarity NPC476353
0.7928 Intermediate Similarity NPC125732
0.7926 Intermediate Similarity NPC16188
0.791 Intermediate Similarity NPC266741
0.7907 Intermediate Similarity NPC328070
0.7895 Intermediate Similarity NPC83289
0.7895 Intermediate Similarity NPC189724
0.7895 Intermediate Similarity NPC212850
0.7891 Intermediate Similarity NPC474091
0.7879 Intermediate Similarity NPC322526
0.7879 Intermediate Similarity NPC471201
0.7852 Intermediate Similarity NPC81026
0.785 Intermediate Similarity NPC177420
0.785 Intermediate Similarity NPC280347
0.784 Intermediate Similarity NPC307020
0.7829 Intermediate Similarity NPC45191
0.7812 Intermediate Similarity NPC271808
0.7805 Intermediate Similarity NPC160120
0.7805 Intermediate Similarity NPC471308
0.7805 Intermediate Similarity NPC289330
0.7805 Intermediate Similarity NPC53596
0.7805 Intermediate Similarity NPC17388
0.7803 Intermediate Similarity NPC473055
0.7803 Intermediate Similarity NPC473052
0.7778 Intermediate Similarity NPC290566
0.7778 Intermediate Similarity NPC62101
0.7778 Intermediate Similarity NPC95733
0.7778 Intermediate Similarity NPC145638
0.7769 Intermediate Similarity NPC274732
0.7769 Intermediate Similarity NPC471953
0.7757 Intermediate Similarity NPC25493
0.7757 Intermediate Similarity NPC113460
0.7754 Intermediate Similarity NPC473491
0.7748 Intermediate Similarity NPC473388
0.7744 Intermediate Similarity NPC48202
0.7742 Intermediate Similarity NPC284078
0.7739 Intermediate Similarity NPC211551
0.7727 Intermediate Similarity NPC161972
0.7727 Intermediate Similarity NPC303045
0.7717 Intermediate Similarity NPC29477
0.7704 Intermediate Similarity NPC326241
0.7698 Intermediate Similarity NPC211218
0.7698 Intermediate Similarity NPC233702
0.7692 Intermediate Similarity NPC114102
0.7692 Intermediate Similarity NPC475735
0.7686 Intermediate Similarity NPC10286
0.7686 Intermediate Similarity NPC37302
0.7686 Intermediate Similarity NPC213
0.7685 Intermediate Similarity NPC318325
0.7685 Intermediate Similarity NPC258219
0.7685 Intermediate Similarity NPC242240
0.7685 Intermediate Similarity NPC123273
0.7681 Intermediate Similarity NPC245974
0.7664 Intermediate Similarity NPC23167
0.7664 Intermediate Similarity NPC247298
0.7661 Intermediate Similarity NPC263835
0.7658 Intermediate Similarity NPC26244
0.7647 Intermediate Similarity NPC163674
0.7647 Intermediate Similarity NPC227553
0.7643 Intermediate Similarity NPC56685
0.7643 Intermediate Similarity NPC262166
0.7643 Intermediate Similarity NPC202198
0.7643 Intermediate Similarity NPC261934
0.7643 Intermediate Similarity NPC5194
0.7634 Intermediate Similarity NPC470392
0.7626 Intermediate Similarity NPC476743
0.7623 Intermediate Similarity NPC106551
0.7623 Intermediate Similarity NPC281686
0.7623 Intermediate Similarity NPC188867
0.76 Intermediate Similarity NPC473050
0.76 Intermediate Similarity NPC473051
0.7597 Intermediate Similarity NPC477839
0.7597 Intermediate Similarity NPC251571
0.7597 Intermediate Similarity NPC153990
0.7594 Intermediate Similarity NPC6913
0.7589 Intermediate Similarity NPC33168
0.7576 Intermediate Similarity NPC6854
0.7576 Intermediate Similarity NPC313737
0.7576 Intermediate Similarity NPC285078
0.7571 Intermediate Similarity NPC476744
0.757 Intermediate Similarity NPC197783
0.7568 Intermediate Similarity NPC151715
0.7568 Intermediate Similarity NPC58674
0.7565 Intermediate Similarity NPC68055
0.7557 Intermediate Similarity NPC473724
0.7554 Intermediate Similarity NPC132771
0.7545 Intermediate Similarity NPC270547
0.7545 Intermediate Similarity NPC304541
0.7544 Intermediate Similarity NPC29601
0.7537 Intermediate Similarity NPC242159
0.7537 Intermediate Similarity NPC313694
0.7535 Intermediate Similarity NPC244509
0.7523 Intermediate Similarity NPC98772
0.7521 Intermediate Similarity NPC309808
0.7521 Intermediate Similarity NPC474544
0.7521 Intermediate Similarity NPC1986
0.7519 Intermediate Similarity NPC218530
0.75 Intermediate Similarity NPC184169
0.75 Intermediate Similarity NPC130595
0.75 Intermediate Similarity NPC93882
0.75 Intermediate Similarity NPC214869
0.7481 Intermediate Similarity NPC195749
0.7481 Intermediate Similarity NPC52029
0.7481 Intermediate Similarity NPC35961
0.748 Intermediate Similarity NPC471314
0.748 Intermediate Similarity NPC471315
0.748 Intermediate Similarity NPC258992
0.7477 Intermediate Similarity NPC175313
0.7477 Intermediate Similarity NPC210497
0.7477 Intermediate Similarity NPC94139
0.7477 Intermediate Similarity NPC147284
0.7477 Intermediate Similarity NPC248817
0.7477 Intermediate Similarity NPC138117
0.7477 Intermediate Similarity NPC325292
0.7477 Intermediate Similarity NPC3358
0.7477 Intermediate Similarity NPC306884
0.7477 Intermediate Similarity NPC162314
0.7465 Intermediate Similarity NPC476742
0.7465 Intermediate Similarity NPC39431
0.746 Intermediate Similarity NPC324702
0.7455 Intermediate Similarity NPC226438
0.7455 Intermediate Similarity NPC300017
0.7445 Intermediate Similarity NPC474128
0.744 Intermediate Similarity NPC239697
0.7438 Intermediate Similarity NPC146422
0.7434 Intermediate Similarity NPC82664
0.7434 Intermediate Similarity NPC292730
0.7434 Intermediate Similarity NPC311242
0.7434 Intermediate Similarity NPC216520
0.7434 Intermediate Similarity NPC132271
0.7431 Intermediate Similarity NPC323336
0.7431 Intermediate Similarity NPC326349
0.7424 Intermediate Similarity NPC308885
0.7424 Intermediate Similarity NPC257390
0.7424 Intermediate Similarity NPC255550
0.7414 Intermediate Similarity NPC196479
0.7413 Intermediate Similarity NPC476741
0.7413 Intermediate Similarity NPC473580
0.7411 Intermediate Similarity NPC27323
0.7411 Intermediate Similarity NPC316301
0.7405 Intermediate Similarity NPC155838
0.7398 Intermediate Similarity NPC303370
0.7391 Intermediate Similarity NPC228400
0.7391 Intermediate Similarity NPC214200
0.7388 Intermediate Similarity NPC120114
0.7388 Intermediate Similarity NPC71888
0.7387 Intermediate Similarity NPC45040
0.7385 Intermediate Similarity NPC301713
0.7383 Intermediate Similarity NPC265146
0.7383 Intermediate Similarity NPC124436
0.7381 Intermediate Similarity NPC321133
0.7381 Intermediate Similarity NPC41801

  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 NPC317254 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
0.8833 High Similarity NPD7451 Discontinued
0.8629 High Similarity NPD5729 Clinical (unspecified phase)
0.8583 High Similarity NPD3676 Clinical (unspecified phase)
0.8468 Intermediate Similarity NPD3136 Phase 2
0.8288 Intermediate Similarity NPD9610 Approved
0.8288 Intermediate Similarity NPD9608 Approved
0.8154 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.8154 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD2229 Approved
0.812 Intermediate Similarity NPD2234 Approved
0.812 Intermediate Similarity NPD2228 Approved
0.8092 Intermediate Similarity NPD7450 Phase 2
0.803 Intermediate Similarity NPD7978 Discontinued
0.7886 Intermediate Similarity NPD3421 Phase 3
0.7852 Intermediate Similarity NPD7066 Clinical (unspecified phase)
0.7851 Intermediate Similarity NPD318 Approved
0.7851 Intermediate Similarity NPD317 Approved
0.784 Intermediate Similarity NPD4659 Approved
0.7826 Intermediate Similarity NPD1444 Approved
0.7826 Intermediate Similarity NPD1445 Approved
0.7787 Intermediate Similarity NPD5303 Approved
0.7787 Intermediate Similarity NPD5304 Approved
0.7778 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD2561 Approved
0.776 Intermediate Similarity NPD2562 Approved
0.7727 Intermediate Similarity NPD2934 Approved
0.7727 Intermediate Similarity NPD2933 Approved
0.771 Intermediate Similarity NPD6346 Approved
0.7705 Intermediate Similarity NPD16 Approved
0.7705 Intermediate Similarity NPD856 Approved
0.7699 Intermediate Similarity NPD4760 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD6682 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD2859 Approved
0.7658 Intermediate Similarity NPD2860 Approved
0.7643 Intermediate Similarity NPD7523 Phase 3
0.7642 Intermediate Similarity NPD1759 Phase 1
0.7627 Intermediate Similarity NPD1792 Phase 2
0.7623 Intermediate Similarity NPD9568 Approved
0.7611 Intermediate Similarity NPD3020 Approved
0.7603 Intermediate Similarity NPD9614 Approved
0.7603 Intermediate Similarity NPD9618 Approved
0.7581 Intermediate Similarity NPD4093 Discontinued
0.7578 Intermediate Similarity NPD4103 Phase 2
0.7578 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD7303 Discontinued
0.7561 Intermediate Similarity NPD1758 Phase 1
0.7545 Intermediate Similarity NPD6690 Approved
0.7537 Intermediate Similarity NPD3555 Approved
0.7537 Intermediate Similarity NPD3552 Approved
0.7537 Intermediate Similarity NPD3554 Approved
0.7537 Intermediate Similarity NPD3553 Approved
0.752 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2674 Phase 3
0.75 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD3053 Approved
0.7442 Intermediate Similarity NPD3055 Approved
0.7438 Intermediate Similarity NPD9379 Approved
0.7438 Intermediate Similarity NPD9377 Approved
0.7424 Intermediate Similarity NPD3145 Approved
0.7424 Intermediate Similarity NPD3144 Approved
0.7411 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD255 Approved
0.7398 Intermediate Similarity NPD256 Approved
0.7387 Intermediate Similarity NPD1814 Approved
0.7387 Intermediate Similarity NPD1812 Approved
0.7383 Intermediate Similarity NPD111 Approved
0.7381 Intermediate Similarity NPD2668 Approved
0.7381 Intermediate Similarity NPD2667 Approved
0.7379 Intermediate Similarity NPD7495 Discontinued
0.7376 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7477 Discontinued
0.7364 Intermediate Similarity NPD5310 Approved
0.7364 Intermediate Similarity NPD5311 Approved
0.7328 Intermediate Similarity NPD855 Approved
0.7328 Intermediate Similarity NPD854 Approved
0.7328 Intermediate Similarity NPD3635 Approved
0.7328 Intermediate Similarity NPD3637 Approved
0.7328 Intermediate Similarity NPD3636 Approved
0.7324 Intermediate Similarity NPD6390 Discontinued
0.7323 Intermediate Similarity NPD3143 Discontinued
0.7317 Intermediate Similarity NPD1793 Approved
0.7317 Intermediate Similarity NPD1791 Approved
0.7317 Intermediate Similarity NPD475 Phase 2
0.731 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD1131 Approved
0.7308 Intermediate Similarity NPD1135 Approved
0.7308 Intermediate Similarity NPD1129 Approved
0.7308 Intermediate Similarity NPD1133 Approved
0.7308 Intermediate Similarity NPD1134 Approved
0.7295 Intermediate Similarity NPD821 Approved
0.7287 Intermediate Similarity NPD1669 Approved
0.7287 Intermediate Similarity NPD9622 Approved
0.7287 Intermediate Similarity NPD3685 Discontinued
0.728 Intermediate Similarity NPD9613 Approved
0.728 Intermediate Similarity NPD9616 Approved
0.728 Intermediate Similarity NPD9615 Approved
0.7273 Intermediate Similarity NPD2606 Approved
0.7273 Intermediate Similarity NPD2605 Approved
0.7266 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD8019 Approved
0.7252 Intermediate Similarity NPD2195 Approved
0.7252 Intermediate Similarity NPD2194 Approved
0.7244 Intermediate Similarity NPD1751 Approved
0.7239 Intermediate Similarity NPD839 Approved
0.7239 Intermediate Similarity NPD840 Approved
0.7222 Intermediate Similarity NPD316 Approved
0.7218 Intermediate Similarity NPD5155 Approved
0.7218 Intermediate Similarity NPD5156 Approved
0.7218 Intermediate Similarity NPD2372 Approved
0.7217 Intermediate Similarity NPD9612 Approved
0.7217 Intermediate Similarity NPD9273 Approved
0.7217 Intermediate Similarity NPD9611 Approved
0.7217 Intermediate Similarity NPD9609 Approved
0.7209 Intermediate Similarity NPD5108 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD2568 Approved
0.7203 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD7526 Approved
0.7203 Intermediate Similarity NPD52 Approved
0.72 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD7153 Discontinued
0.719 Intermediate Similarity NPD3022 Approved
0.719 Intermediate Similarity NPD3021 Approved
0.7179 Intermediate Similarity NPD4817 Approved
0.7179 Intermediate Similarity NPD940 Approved
0.7179 Intermediate Similarity NPD846 Approved
0.7179 Intermediate Similarity NPD4818 Approved
0.7168 Intermediate Similarity NPD845 Approved
0.7167 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6406 Approved
0.7164 Intermediate Similarity NPD598 Approved
0.7164 Intermediate Similarity NPD601 Approved
0.7164 Intermediate Similarity NPD597 Approved
0.7143 Intermediate Similarity NPD3594 Approved
0.7143 Intermediate Similarity NPD3595 Approved
0.7133 Intermediate Similarity NPD4739 Approved
0.7133 Intermediate Similarity NPD8303 Discontinued
0.7131 Intermediate Similarity NPD4254 Approved
0.7131 Intermediate Similarity NPD4253 Approved
0.7111 Intermediate Similarity NPD1132 Approved
0.7111 Intermediate Similarity NPD1136 Approved
0.7111 Intermediate Similarity NPD5745 Approved
0.7111 Intermediate Similarity NPD1130 Approved
0.7111 Intermediate Similarity NPD6405 Approved
0.7111 Intermediate Similarity NPD6407 Approved
0.7111 Intermediate Similarity NPD1423 Approved
0.7109 Intermediate Similarity NPD9381 Approved
0.7109 Intermediate Similarity NPD9384 Approved
0.7105 Intermediate Similarity NPD4814 Discontinued
0.7099 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD3400 Discontinued
0.7083 Intermediate Similarity NPD4186 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD3054 Approved
0.708 Intermediate Similarity NPD3052 Approved
0.708 Intermediate Similarity NPD2157 Approved
0.708 Intermediate Similarity NPD5314 Approved
0.7068 Intermediate Similarity NPD9569 Approved
0.7068 Intermediate Similarity NPD1712 Approved
0.7063 Intermediate Similarity NPD3123 Discovery
0.7059 Intermediate Similarity NPD315 Approved
0.7059 Intermediate Similarity NPD10 Approved
0.7059 Intermediate Similarity NPD309 Approved
0.7059 Intermediate Similarity NPD310 Approved
0.7059 Intermediate Similarity NPD314 Approved
0.7059 Intermediate Similarity NPD311 Approved
0.7059 Intermediate Similarity NPD179 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD1980 Approved
0.7054 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD1983 Approved
0.7054 Intermediate Similarity NPD1981 Approved
0.705 Intermediate Similarity NPD2161 Phase 2
0.7043 Intermediate Similarity NPD844 Approved
0.7043 Intermediate Similarity NPD1809 Phase 2
0.7034 Intermediate Similarity NPD7131 Phase 3
0.7023 Intermediate Similarity NPD6582 Phase 2
0.7023 Intermediate Similarity NPD6583 Phase 3
0.7021 Intermediate Similarity NPD2458 Approved
0.7021 Intermediate Similarity NPD2460 Phase 3
0.7021 Intermediate Similarity NPD2459 Approved
0.6992 Remote Similarity NPD602 Approved
0.6992 Remote Similarity NPD9619 Approved
0.6992 Remote Similarity NPD9621 Approved
0.6992 Remote Similarity NPD599 Approved
0.6992 Remote Similarity NPD9620 Approved
0.6992 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6985 Remote Similarity NPD259 Phase 1
0.6985 Remote Similarity NPD829 Discontinued
0.6983 Remote Similarity NPD288 Approved
0.698 Remote Similarity NPD5772 Approved
0.698 Remote Similarity NPD5773 Approved
0.6977 Remote Similarity NPD7342 Discontinued
0.6963 Remote Similarity NPD5746 Approved
0.6963 Remote Similarity NPD1024 Discontinued
0.6959 Remote Similarity NPD7438 Suspended
0.6949 Remote Similarity NPD3028 Approved
0.6947 Remote Similarity NPD6624 Discontinued

  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