Structure

Physi-Chem Properties

Molecular Weight:  588.3
Volume:  634.709
LogP:  9.749
LogD:  5.065
LogS:  -3.955
# Rotatable Bonds:  7
TPSA:  90.5
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.14
Synthetic Accessibility Score:  3.496
Fsp3:  0.263
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:  -5.969
MDCK Permeability:  1.1547693247848656e-05
Pgp-inhibitor:  0.976
Pgp-substrate:  0.626
Human Intestinal Absorption (HIA):  0.88
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  82.14887237548828%
Volume Distribution (VD):  2.793
Pgp-substrate:  8.688300132751465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.687
CYP1A2-substrate:  0.838
CYP2C19-inhibitor:  0.886
CYP2C19-substrate:  0.079
CYP2C9-inhibitor:  0.816
CYP2C9-substrate:  0.916
CYP2D6-inhibitor:  0.167
CYP2D6-substrate:  0.896
CYP3A4-inhibitor:  0.093
CYP3A4-substrate:  0.31

ADMET: Excretion

Clearance (CL):  5.533
Half-life (T1/2):  0.013

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.851
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.507
Rat Oral Acute Toxicity:  0.965
Maximum Recommended Daily Dose:  0.856
Skin Sensitization:  0.746
Carcinogencity:  0.049
Eye Corrosion:  0.003
Eye Irritation:  0.183
Respiratory Toxicity:  0.865

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

  Natural Product: NPC202503

Natural Product ID:  NPC202503
Common Name*:   Bismurrayafoline B
IUPAC Name:   2-[1-hydroxy-7-methoxy-3-methyl-8-(3-methylbut-2-enyl)-9H-carbazol-2-yl]-7-methoxy-3-methyl-8-(3-methylbut-2-enyl)-9H-carbazol-1-ol
Synonyms:  
Standard InCHIKey:  STVAUJYOJBWBNS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C38H40N2O4/c1-19(2)9-11-25-29(43-7)15-13-23-27-17-21(5)31(37(41)35(27)39-33(23)25)32-22(6)18-28-24-14-16-30(44-8)26(12-10-20(3)4)34(24)40-36(28)38(32)42/h9-10,13-18,39-42H,11-12H2,1-8H3
SMILES:  COc1ccc2c(c1CC=C(C)C)[nH]c1c2cc(c(c1O)c1c(C)cc2c(c1O)[nH]c1c2ccc(c1CC=C(C)C)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510968
PubChem CID:   375145
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota stem bark;fruit n.a. n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota root bark Kuantaochi, Nantou Hsien, Taiwan n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3118 Murraya euchrestifolia Species Rutaceae 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[525629]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[525629]

☑ 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 NPC202503 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
0.922 High Similarity NPC473179
0.9061 High Similarity NPC473182
0.8927 High Similarity NPC473180
0.8915 High Similarity NPC473185
0.8879 High Similarity NPC477531
0.8873 High Similarity NPC252251
0.8832 High Similarity NPC209174
0.8829 High Similarity NPC199667
0.878 High Similarity NPC209769
0.878 High Similarity NPC473181
0.8679 High Similarity NPC477532
0.8591 High Similarity NPC473183
0.8584 High Similarity NPC473184
0.8532 High Similarity NPC475253
0.8502 High Similarity NPC193777
0.8495 Intermediate Similarity NPC470930
0.8458 Intermediate Similarity NPC132642
0.8416 Intermediate Similarity NPC277351
0.8404 Intermediate Similarity NPC314552
0.8341 Intermediate Similarity NPC473188
0.8333 Intermediate Similarity NPC243834
0.8333 Intermediate Similarity NPC70956
0.8302 Intermediate Similarity NPC48353
0.8302 Intermediate Similarity NPC94157
0.8287 Intermediate Similarity NPC477533
0.8164 Intermediate Similarity NPC128823
0.8134 Intermediate Similarity NPC475085
0.8134 Intermediate Similarity NPC475112
0.8134 Intermediate Similarity NPC291535
0.8075 Intermediate Similarity NPC201697
0.8068 Intermediate Similarity NPC153042
0.8053 Intermediate Similarity NPC473187
0.8037 Intermediate Similarity NPC86078
0.8019 Intermediate Similarity NPC476106
0.8018 Intermediate Similarity NPC200888
0.8 Intermediate Similarity NPC267423
0.7971 Intermediate Similarity NPC131017
0.796 Intermediate Similarity NPC474798
0.7943 Intermediate Similarity NPC72211
0.7925 Intermediate Similarity NPC162484
0.7902 Intermediate Similarity NPC242928
0.7892 Intermediate Similarity NPC179287
0.788 Intermediate Similarity NPC294620
0.7867 Intermediate Similarity NPC274640
0.7866 Intermediate Similarity NPC89549
0.786 Intermediate Similarity NPC470931
0.7857 Intermediate Similarity NPC227908
0.785 Intermediate Similarity NPC304183
0.7848 Intermediate Similarity NPC51388
0.7847 Intermediate Similarity NPC70259
0.7843 Intermediate Similarity NPC94943
0.7799 Intermediate Similarity NPC205934
0.7799 Intermediate Similarity NPC43787
0.7794 Intermediate Similarity NPC190007
0.7788 Intermediate Similarity NPC280964
0.7788 Intermediate Similarity NPC141915
0.7788 Intermediate Similarity NPC114335
0.7788 Intermediate Similarity NPC11464
0.7778 Intermediate Similarity NPC106833
0.7778 Intermediate Similarity NPC469497
0.7757 Intermediate Similarity NPC223427
0.7745 Intermediate Similarity NPC212535
0.7729 Intermediate Similarity NPC128751
0.7729 Intermediate Similarity NPC246700
0.7723 Intermediate Similarity NPC144452
0.7721 Intermediate Similarity NPC137929
0.7721 Intermediate Similarity NPC164374
0.7672 Intermediate Similarity NPC11408
0.7671 Intermediate Similarity NPC208284
0.7667 Intermediate Similarity NPC475190
0.7664 Intermediate Similarity NPC476044
0.7642 Intermediate Similarity NPC474701
0.7634 Intermediate Similarity NPC225279
0.7628 Intermediate Similarity NPC199277
0.7628 Intermediate Similarity NPC135887
0.7619 Intermediate Similarity NPC39370
0.7613 Intermediate Similarity NPC170114
0.7609 Intermediate Similarity NPC473186
0.7607 Intermediate Similarity NPC475844
0.7607 Intermediate Similarity NPC217554
0.7602 Intermediate Similarity NPC478074
0.7602 Intermediate Similarity NPC471080
0.7602 Intermediate Similarity NPC469592
0.7593 Intermediate Similarity NPC475774
0.7589 Intermediate Similarity NPC208084
0.7585 Intermediate Similarity NPC284141
0.7578 Intermediate Similarity NPC293151
0.757 Intermediate Similarity NPC18487
0.7568 Intermediate Similarity NPC470549
0.7566 Intermediate Similarity NPC118121
0.7565 Intermediate Similarity NPC474688
0.7556 Intermediate Similarity NPC150239
0.7554 Intermediate Similarity NPC6786
0.7546 Intermediate Similarity NPC66815
0.7545 Intermediate Similarity NPC469594
0.7545 Intermediate Similarity NPC184408
0.7535 Intermediate Similarity NPC11017
0.7534 Intermediate Similarity NPC8022
0.7534 Intermediate Similarity NPC470799
0.7511 Intermediate Similarity NPC148409
0.7489 Intermediate Similarity NPC118228
0.7477 Intermediate Similarity NPC285558
0.7469 Intermediate Similarity NPC189079
0.7467 Intermediate Similarity NPC247803
0.7455 Intermediate Similarity NPC475910
0.7454 Intermediate Similarity NPC329747
0.7452 Intermediate Similarity NPC84478
0.7447 Intermediate Similarity NPC131486
0.7437 Intermediate Similarity NPC208522
0.7434 Intermediate Similarity NPC213530
0.7434 Intermediate Similarity NPC46451
0.7434 Intermediate Similarity NPC193267
0.7432 Intermediate Similarity NPC87413
0.7427 Intermediate Similarity NPC133609
0.7416 Intermediate Similarity NPC473189
0.7415 Intermediate Similarity NPC477861
0.7411 Intermediate Similarity NPC235076
0.7409 Intermediate Similarity NPC132385
0.7401 Intermediate Similarity NPC174760
0.7391 Intermediate Similarity NPC478032
0.7389 Intermediate Similarity NPC204446
0.7389 Intermediate Similarity NPC23614
0.7389 Intermediate Similarity NPC100079
0.7384 Intermediate Similarity NPC477066
0.7382 Intermediate Similarity NPC469554
0.7382 Intermediate Similarity NPC132329
0.7378 Intermediate Similarity NPC183407
0.7366 Intermediate Similarity NPC39500
0.7353 Intermediate Similarity NPC478081
0.7343 Intermediate Similarity NPC88363
0.7342 Intermediate Similarity NPC469589
0.7336 Intermediate Similarity NPC478080
0.7336 Intermediate Similarity NPC280272
0.7333 Intermediate Similarity NPC475666
0.7333 Intermediate Similarity NPC42591
0.7321 Intermediate Similarity NPC26679
0.7317 Intermediate Similarity NPC474409
0.7313 Intermediate Similarity NPC303658
0.7308 Intermediate Similarity NPC101543
0.7297 Intermediate Similarity NPC39679
0.7292 Intermediate Similarity NPC81939
0.7284 Intermediate Similarity NPC470126
0.728 Intermediate Similarity NPC477067
0.728 Intermediate Similarity NPC478082
0.728 Intermediate Similarity NPC473540
0.7277 Intermediate Similarity NPC187501
0.7269 Intermediate Similarity NPC169402
0.7265 Intermediate Similarity NPC185782
0.726 Intermediate Similarity NPC72980
0.7253 Intermediate Similarity NPC253580
0.7252 Intermediate Similarity NPC249583
0.7252 Intermediate Similarity NPC4687
0.7244 Intermediate Similarity NPC203168
0.7244 Intermediate Similarity NPC308137
0.7244 Intermediate Similarity NPC310211
0.7237 Intermediate Similarity NPC46561
0.7236 Intermediate Similarity NPC472589
0.7232 Intermediate Similarity NPC123976
0.7232 Intermediate Similarity NPC219664
0.7232 Intermediate Similarity NPC188420
0.7232 Intermediate Similarity NPC167860
0.7231 Intermediate Similarity NPC17437
0.7229 Intermediate Similarity NPC211416
0.7229 Intermediate Similarity NPC167908
0.7225 Intermediate Similarity NPC3207
0.7224 Intermediate Similarity NPC472588
0.722 Intermediate Similarity NPC160898
0.7217 Intermediate Similarity NPC280799
0.7217 Intermediate Similarity NPC314573
0.7217 Intermediate Similarity NPC198503
0.7212 Intermediate Similarity NPC149471
0.7212 Intermediate Similarity NPC266931
0.7212 Intermediate Similarity NPC271215
0.72 Intermediate Similarity NPC9894
0.72 Intermediate Similarity NPC23294
0.7195 Intermediate Similarity NPC476138
0.7195 Intermediate Similarity NPC245816
0.7191 Intermediate Similarity NPC476451
0.7181 Intermediate Similarity NPC116238
0.7176 Intermediate Similarity NPC78284
0.7175 Intermediate Similarity NPC283117
0.7168 Intermediate Similarity NPC316981
0.7163 Intermediate Similarity NPC56618
0.7161 Intermediate Similarity NPC49547
0.7156 Intermediate Similarity NPC303951
0.7156 Intermediate Similarity NPC176127
0.7154 Intermediate Similarity NPC244543
0.7143 Intermediate Similarity NPC295228
0.7143 Intermediate Similarity NPC310118
0.7143 Intermediate Similarity NPC195314
0.7131 Intermediate Similarity NPC270515
0.7124 Intermediate Similarity NPC294375
0.7121 Intermediate Similarity NPC195788
0.7121 Intermediate Similarity NPC237901
0.7117 Intermediate Similarity NPC469440
0.7112 Intermediate Similarity NPC162748
0.711 Intermediate Similarity NPC205403
0.7106 Intermediate Similarity NPC194740
0.7106 Intermediate Similarity NPC476997
0.7106 Intermediate Similarity NPC314954

  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 NPC202503 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
0.8404 Intermediate Similarity NPD5164 Discontinued
0.7752 Intermediate Similarity NPD4502 Phase 2
0.7686 Intermediate Similarity NPD3746 Discontinued
0.7667 Intermediate Similarity NPD8244 Phase 2
0.7573 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7511 Intermediate Similarity NPD5936 Approved
0.7511 Intermediate Similarity NPD5939 Approved
0.75 Intermediate Similarity NPD7558 Phase 2
0.7489 Intermediate Similarity NPD5902 Approved
0.7489 Intermediate Similarity NPD7222 Phase 2
0.7489 Intermediate Similarity NPD5903 Approved
0.7488 Intermediate Similarity NPD8395 Approved
0.7488 Intermediate Similarity NPD8396 Approved
0.7467 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD5530 Phase 1
0.7443 Intermediate Similarity NPD3003 Approved
0.7434 Intermediate Similarity NPD3763 Approved
0.7412 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7453 Approved
0.7409 Intermediate Similarity NPD7452 Approved
0.7376 Intermediate Similarity NPD5658 Approved
0.736 Intermediate Similarity NPD8364 Approved
0.736 Intermediate Similarity NPD8363 Approved
0.7339 Intermediate Similarity NPD6456 Discontinued
0.7325 Intermediate Similarity NPD7678 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7281 Intermediate Similarity NPD3875 Discontinued
0.728 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4511 Phase 1
0.7253 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD5429 Discontinued
0.7252 Intermediate Similarity NPD6290 Phase 2
0.7248 Intermediate Similarity NPD2176 Approved
0.7248 Intermediate Similarity NPD2175 Phase 3
0.7248 Intermediate Similarity NPD2177 Approved
0.7235 Intermediate Similarity NPD7948 Phase 1
0.7231 Intermediate Similarity NPD8358 Approved
0.7225 Intermediate Similarity NPD5612 Discontinued
0.7205 Intermediate Similarity NPD7194 Discontinued
0.7203 Intermediate Similarity NPD6494 Phase 2
0.7179 Intermediate Similarity NPD7555 Discontinued
0.7177 Intermediate Similarity NPD7479 Phase 2
0.717 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1768 Approved
0.7169 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD7395 Discontinued
0.7162 Intermediate Similarity NPD6985 Discontinued
0.713 Intermediate Similarity NPD8403 Phase 1
0.7125 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD8016 Phase 3
0.7123 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD8466 Approved
0.7121 Intermediate Similarity NPD8428 Approved
0.7121 Intermediate Similarity NPD8465 Approved
0.7121 Intermediate Similarity NPD8467 Approved
0.7121 Intermediate Similarity NPD8429 Approved
0.7121 Intermediate Similarity NPD8427 Approved
0.7049 Intermediate Similarity NPD5488 Discontinued
0.7039 Intermediate Similarity NPD7219 Approved
0.7039 Intermediate Similarity NPD7221 Approved
0.7021 Intermediate Similarity NPD7603 Discontinued
0.7018 Intermediate Similarity NPD1038 Approved
0.7011 Intermediate Similarity NPD8459 Approved
0.7011 Intermediate Similarity NPD8426 Approved
0.7011 Intermediate Similarity NPD8460 Approved
0.7011 Intermediate Similarity NPD8425 Approved
0.7004 Intermediate Similarity NPD7567 Approved
0.6991 Remote Similarity NPD7671 Approved
0.6991 Remote Similarity NPD7672 Approved
0.6986 Remote Similarity NPD6861 Clinical (unspecified phase)
0.697 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6968 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6967 Remote Similarity NPD6159 Phase 2
0.6957 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6947 Remote Similarity NPD1392 Approved
0.6934 Remote Similarity NPD3920 Phase 2
0.6931 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5913 Phase 3
0.6923 Remote Similarity NPD7726 Phase 1
0.692 Remote Similarity NPD6975 Discontinued
0.692 Remote Similarity NPD6977 Clinical (unspecified phase)
0.692 Remote Similarity NPD6978 Phase 2
0.6917 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6916 Remote Similarity NPD2916 Discontinued
0.6909 Remote Similarity NPD6590 Discontinued
0.6909 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6907 Remote Similarity NPD6976 Clinical (unspecified phase)
0.6907 Remote Similarity NPD7586 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6150 Discontinued
0.6889 Remote Similarity NPD2920 Discontinued
0.6885 Remote Similarity NPD7417 Discontinued
0.6864 Remote Similarity NPD1304 Clinical (unspecified phase)
0.686 Remote Similarity NPD4454 Phase 2
0.6849 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6838 Remote Similarity NPD6455 Phase 3
0.6837 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6836 Remote Similarity NPD8284 Discontinued
0.6833 Remote Similarity NPD4418 Discontinued
0.6826 Remote Similarity NPD5067 Phase 2
0.6826 Remote Similarity NPD5066 Phase 2
0.6825 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6736 Discontinued
0.682 Remote Similarity NPD5256 Discontinued
0.6818 Remote Similarity NPD2951 Discontinued
0.681 Remote Similarity NPD1325 Approved
0.681 Remote Similarity NPD1326 Approved
0.6809 Remote Similarity NPD6717 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7181 Phase 3
0.6798 Remote Similarity NPD8091 Phase 3
0.6797 Remote Similarity NPD7069 Discontinued
0.6797 Remote Similarity NPD3816 Phase 1
0.6797 Remote Similarity NPD3815 Phase 1
0.6795 Remote Similarity NPD5632 Approved
0.6795 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6791 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6789 Remote Similarity NPD6473 Phase 1
0.6789 Remote Similarity NPD6716 Phase 1
0.6789 Remote Similarity NPD8431 Approved
0.6787 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8442 Discontinued
0.6784 Remote Similarity NPD4795 Phase 2
0.6778 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6772 Remote Similarity NPD7955 Approved
0.6772 Remote Similarity NPD7956 Approved
0.677 Remote Similarity NPD6208 Discontinued
0.6766 Remote Similarity NPD8349 Phase 1
0.6765 Remote Similarity NPD8524 Approved
0.6763 Remote Similarity NPD1505 Phase 2
0.6754 Remote Similarity NPD4305 Clinical (unspecified phase)
0.6753 Remote Similarity NPD6220 Phase 3
0.6751 Remote Similarity NPD1856 Discontinued
0.6751 Remote Similarity NPD6995 Phase 1
0.6744 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6742 Remote Similarity NPD3963 Phase 1
0.6742 Remote Similarity NPD8286 Phase 2
0.6737 Remote Similarity NPD5930 Phase 3
0.6736 Remote Similarity NPD4885 Approved
0.6728 Remote Similarity NPD8489 Phase 1
0.6727 Remote Similarity NPD2565 Phase 2
0.6727 Remote Similarity NPD2564 Approved
0.6726 Remote Similarity NPD6550 Discontinued
0.6726 Remote Similarity NPD5512 Phase 3
0.6724 Remote Similarity NPD4927 Discontinued
0.6722 Remote Similarity NPD5479 Discontinued
0.6721 Remote Similarity NPD7853 Phase 2
0.6711 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6988 Phase 1
0.6694 Remote Similarity NPD7688 Phase 1
0.6693 Remote Similarity NPD5482 Discontinued
0.6693 Remote Similarity NPD3986 Discontinued
0.6681 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6991 Approved
0.6667 Remote Similarity NPD3923 Approved
0.6667 Remote Similarity NPD3924 Approved
0.6667 Remote Similarity NPD3922 Approved
0.6667 Remote Similarity NPD7073 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7674 Phase 3
0.6667 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7675 Phase 3
0.6667 Remote Similarity NPD3921 Approved
0.6653 Remote Similarity NPD6517 Phase 3
0.6653 Remote Similarity NPD3006 Discontinued
0.6652 Remote Similarity NPD6202 Discontinued
0.6641 Remote Similarity NPD7803 Approved
0.664 Remote Similarity NPD6742 Phase 2
0.664 Remote Similarity NPD6743 Phase 2
0.6639 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6639 Remote Similarity NPD4881 Clinical (unspecified phase)
0.6637 Remote Similarity NPD3825 Phase 3
0.6637 Remote Similarity NPD802 Phase 2
0.6636 Remote Similarity NPD4203 Approved
0.6636 Remote Similarity NPD4204 Approved
0.6627 Remote Similarity NPD7068 Approved
0.6627 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6243 Phase 3
0.6627 Remote Similarity NPD6244 Phase 3
0.6627 Remote Similarity NPD7067 Approved
0.6622 Remote Similarity NPD5003 Discontinued
0.6609 Remote Similarity NPD5416 Discontinued
0.6608 Remote Similarity NPD1740 Approved
0.6608 Remote Similarity NPD1739 Approved
0.6607 Remote Similarity NPD3810 Clinical (unspecified phase)
0.6605 Remote Similarity NPD4354 Approved
0.6602 Remote Similarity NPD7169 Suspended
0.66 Remote Similarity NPD5483 Clinical (unspecified phase)
0.66 Remote Similarity NPD6230 Discontinued
0.6598 Remote Similarity NPD3263 Phase 3
0.6596 Remote Similarity NPD6140 Clinical (unspecified phase)
0.6595 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6592 Remote Similarity NPD6569 Phase 2
0.6591 Remote Similarity NPD7691 Clinical (unspecified phase)
0.6581 Remote Similarity NPD3330 Phase 1
0.6578 Remote Similarity NPD6449 Clinical (unspecified phase)
0.6577 Remote Similarity NPD3342 Phase 2
0.6577 Remote Similarity NPD7630 Phase 3
0.6577 Remote Similarity NPD7628 Phase 3
0.6577 Remote Similarity NPD7629 Clinical (unspecified phase)

  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