Structure

Physi-Chem Properties

Molecular Weight:  690.38
Volume:  722.837
LogP:  5.527
LogD:  4.305
LogS:  -4.6
# Rotatable Bonds:  5
TPSA:  100.03
# H-Bond Aceptor:  9
# H-Bond Donor:  2
# Rings:  8
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.202
Synthetic Accessibility Score:  6.262
Fsp3:  0.476
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:  -5.589
MDCK Permeability:  3.292051042080857e-05
Pgp-inhibitor:  0.989
Pgp-substrate:  0.95
Human Intestinal Absorption (HIA):  0.554
20% Bioavailability (F20%):  0.078
30% Bioavailability (F30%):  0.186

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.809
Plasma Protein Binding (PPB):  78.55085754394531%
Volume Distribution (VD):  1.822
Pgp-substrate:  14.035309791564941%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.282
CYP2C19-inhibitor:  0.496
CYP2C19-substrate:  0.955
CYP2C9-inhibitor:  0.273
CYP2C9-substrate:  0.249
CYP2D6-inhibitor:  0.845
CYP2D6-substrate:  0.885
CYP3A4-inhibitor:  0.877
CYP3A4-substrate:  0.943

ADMET: Excretion

Clearance (CL):  8.864
Half-life (T1/2):  0.012

ADMET: Toxicity

hERG Blockers:  0.779
Human Hepatotoxicity (H-HT):  0.837
Drug-inuced Liver Injury (DILI):  0.942
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.992
Maximum Recommended Daily Dose:  1.0
Skin Sensitization:  0.2
Carcinogencity:  0.252
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.991

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

  Natural Product: NPC33949

Natural Product ID:  NPC33949
Common Name*:   Bisnicalaterine A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  TYYBJRHYBIULFL-STVOPARKSA-N
Standard InCHI:  InChI=1S/C42H50N4O5/c1-7-23-21-44(3)33-18-29-25-13-9-11-15-31(25)43-39(29)35(17-27(23)37(33)41(48)50-5)46-32-16-12-10-14-26(32)30-19-34-38(42(49)51-6)28(20-36(47)40(30)46)24(8-2)22-45(34)4/h7-16,27-28,33-38,43,47H,17-22H2,1-6H3/b23-7-,24-8-/t27-,28-,33+,34+,35-,36-,37+,38+/m1/s1
SMILES:  C/C=C1/CN(C)[C@@H]2[C@H]([C@@H]1C[C@@H](O)c1c(C2)c2c(n1[C@@H]1C[C@@H]3/C(=CC)/CN([C@H]([C@H]3C(=O)OC)Cc3c1[nH]c1c3cccc1)C)cccc2)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077123
PubChem CID:   46881335
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002744] Vobasan alkaloids

*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
NPO15819 Hunteria zeylanica Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19388660]
NPO15819 Hunteria zeylanica Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[21524573]
NPO15819 Hunteria zeylanica Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[28362501]
NPO15819 Hunteria zeylanica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15819 Hunteria zeylanica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15819 Hunteria zeylanica Species Apocynaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 16.2 ug.mL-1 PMID[555284]
NPT389 Cell Line RPMI-8226 Homo sapiens IC50 = 31.3 ug.mL-1 PMID[555284]
NPT405 Cell Line NCI-H226 Homo sapiens IC50 = 28.1 ug.mL-1 PMID[555284]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 21.9 ug.mL-1 PMID[555284]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 38.0 ug.mL-1 PMID[555284]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 16200.0 nM PMID[555285]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4360.0 nM PMID[555285]
NPT2 Others Unspecified Ratio IC50 = 3.7 n.a. PMID[555285]

☑ 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 NPC33949 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
0.8134 Intermediate Similarity NPC199851
0.8134 Intermediate Similarity NPC254240
0.8134 Intermediate Similarity NPC128265
0.8134 Intermediate Similarity NPC312870
0.8134 Intermediate Similarity NPC294909
0.8048 Intermediate Similarity NPC49196
0.8048 Intermediate Similarity NPC249150
0.8048 Intermediate Similarity NPC313985
0.8048 Intermediate Similarity NPC195461
0.8048 Intermediate Similarity NPC79129
0.8048 Intermediate Similarity NPC81654
0.8038 Intermediate Similarity NPC52557
0.8 Intermediate Similarity NPC175474
0.7991 Intermediate Similarity NPC477065
0.7982 Intermediate Similarity NPC478157
0.7952 Intermediate Similarity NPC50503
0.7952 Intermediate Similarity NPC102008
0.7951 Intermediate Similarity NPC472323
0.7936 Intermediate Similarity NPC221100
0.7936 Intermediate Similarity NPC234078
0.7919 Intermediate Similarity NPC52254
0.7902 Intermediate Similarity NPC21638
0.7887 Intermediate Similarity NPC193761
0.7873 Intermediate Similarity NPC281049
0.7867 Intermediate Similarity NPC24370
0.7867 Intermediate Similarity NPC319232
0.7864 Intermediate Similarity NPC476114
0.7857 Intermediate Similarity NPC245916
0.7857 Intermediate Similarity NPC475271
0.7851 Intermediate Similarity NPC54803
0.7851 Intermediate Similarity NPC321592
0.785 Intermediate Similarity NPC165599
0.7841 Intermediate Similarity NPC223409
0.7834 Intermediate Similarity NPC478158
0.7833 Intermediate Similarity NPC15840
0.7832 Intermediate Similarity NPC261251
0.7797 Intermediate Similarity NPC100547
0.7793 Intermediate Similarity NPC82070
0.7788 Intermediate Similarity NPC214142
0.7788 Intermediate Similarity NPC472112
0.7763 Intermediate Similarity NPC322135
0.7763 Intermediate Similarity NPC95240
0.7756 Intermediate Similarity NPC472108
0.7756 Intermediate Similarity NPC139291
0.7753 Intermediate Similarity NPC118559
0.7753 Intermediate Similarity NPC34580
0.7753 Intermediate Similarity NPC124920
0.7753 Intermediate Similarity NPC304307
0.7751 Intermediate Similarity NPC472097
0.7749 Intermediate Similarity NPC57453
0.7748 Intermediate Similarity NPC312645
0.7742 Intermediate Similarity NPC244741
0.774 Intermediate Similarity NPC63199
0.774 Intermediate Similarity NPC111602
0.774 Intermediate Similarity NPC102338
0.774 Intermediate Similarity NPC196251
0.7739 Intermediate Similarity NPC473105
0.7729 Intermediate Similarity NPC14288
0.7727 Intermediate Similarity NPC75634
0.7718 Intermediate Similarity NPC472119
0.7714 Intermediate Similarity NPC472113
0.7708 Intermediate Similarity NPC478080
0.7703 Intermediate Similarity NPC74969
0.7699 Intermediate Similarity NPC229893
0.7696 Intermediate Similarity NPC474192
0.7696 Intermediate Similarity NPC475720
0.7692 Intermediate Similarity NPC89508
0.7692 Intermediate Similarity NPC472291
0.7675 Intermediate Similarity NPC476491
0.767 Intermediate Similarity NPC472109
0.767 Intermediate Similarity NPC472110
0.7662 Intermediate Similarity NPC284888
0.7662 Intermediate Similarity NPC323752
0.7639 Intermediate Similarity NPC476874
0.7634 Intermediate Similarity NPC473310
0.7617 Intermediate Similarity NPC477066
0.7615 Intermediate Similarity NPC238457
0.7613 Intermediate Similarity NPC229348
0.761 Intermediate Similarity NPC219336
0.7609 Intermediate Similarity NPC326363
0.7605 Intermediate Similarity NPC107836
0.7602 Intermediate Similarity NPC82370
0.7596 Intermediate Similarity NPC472107
0.7596 Intermediate Similarity NPC79062
0.7595 Intermediate Similarity NPC81939
0.7591 Intermediate Similarity NPC162860
0.7589 Intermediate Similarity NPC472285
0.7586 Intermediate Similarity NPC323198
0.7585 Intermediate Similarity NPC478081
0.7585 Intermediate Similarity NPC143533
0.7585 Intermediate Similarity NPC477067
0.7585 Intermediate Similarity NPC478082
0.7574 Intermediate Similarity NPC475816
0.7573 Intermediate Similarity NPC469896
0.7571 Intermediate Similarity NPC321708
0.757 Intermediate Similarity NPC141454
0.7565 Intermediate Similarity NPC253580
0.7563 Intermediate Similarity NPC475666
0.7561 Intermediate Similarity NPC326575
0.7561 Intermediate Similarity NPC15573
0.7561 Intermediate Similarity NPC183662
0.7561 Intermediate Similarity NPC217372
0.7557 Intermediate Similarity NPC475422
0.7557 Intermediate Similarity NPC234999
0.7556 Intermediate Similarity NPC174788
0.7556 Intermediate Similarity NPC469594
0.7554 Intermediate Similarity NPC325976
0.7554 Intermediate Similarity NPC33064
0.7554 Intermediate Similarity NPC245055
0.7548 Intermediate Similarity NPC258480
0.7545 Intermediate Similarity NPC469928
0.7545 Intermediate Similarity NPC330009
0.7545 Intermediate Similarity NPC148183
0.7545 Intermediate Similarity NPC152768
0.7536 Intermediate Similarity NPC329858
0.7533 Intermediate Similarity NPC471506
0.7532 Intermediate Similarity NPC470784
0.7531 Intermediate Similarity NPC17437
0.753 Intermediate Similarity NPC471303
0.7523 Intermediate Similarity NPC476098
0.7522 Intermediate Similarity NPC470126
0.7522 Intermediate Similarity NPC476492
0.7521 Intermediate Similarity NPC329982
0.7512 Intermediate Similarity NPC472210
0.7512 Intermediate Similarity NPC472122
0.7512 Intermediate Similarity NPC269886
0.7512 Intermediate Similarity NPC24594
0.7512 Intermediate Similarity NPC247735
0.7512 Intermediate Similarity NPC472295
0.7512 Intermediate Similarity NPC81802
0.75 Intermediate Similarity NPC54420
0.75 Intermediate Similarity NPC241024
0.75 Intermediate Similarity NPC472123
0.749 Intermediate Similarity NPC469734
0.7489 Intermediate Similarity NPC472099
0.7477 Intermediate Similarity NPC19692
0.7477 Intermediate Similarity NPC220151
0.7476 Intermediate Similarity NPC66210
0.7476 Intermediate Similarity NPC478077
0.7467 Intermediate Similarity NPC36405
0.7466 Intermediate Similarity NPC87755
0.7465 Intermediate Similarity NPC55493
0.7465 Intermediate Similarity NPC249040
0.7465 Intermediate Similarity NPC214428
0.7464 Intermediate Similarity NPC472294
0.7458 Intermediate Similarity NPC82472
0.7458 Intermediate Similarity NPC41679
0.7456 Intermediate Similarity NPC474896
0.7455 Intermediate Similarity NPC277350
0.7455 Intermediate Similarity NPC469592
0.7455 Intermediate Similarity NPC54744
0.7455 Intermediate Similarity NPC471080
0.7453 Intermediate Similarity NPC469501
0.7453 Intermediate Similarity NPC314333
0.7453 Intermediate Similarity NPC469470
0.7452 Intermediate Similarity NPC314394
0.7438 Intermediate Similarity NPC317430
0.7438 Intermediate Similarity NPC14812
0.7432 Intermediate Similarity NPC469743
0.7431 Intermediate Similarity NPC475506
0.7425 Intermediate Similarity NPC475859
0.7425 Intermediate Similarity NPC475969
0.7424 Intermediate Similarity NPC31097
0.7422 Intermediate Similarity NPC477979
0.7416 Intermediate Similarity NPC472104
0.7415 Intermediate Similarity NPC28945
0.7415 Intermediate Similarity NPC184680
0.7415 Intermediate Similarity NPC285343
0.7411 Intermediate Similarity NPC475778
0.7411 Intermediate Similarity NPC472098
0.7404 Intermediate Similarity NPC472105
0.7404 Intermediate Similarity NPC187827
0.7398 Intermediate Similarity NPC478006
0.7397 Intermediate Similarity NPC155143
0.7397 Intermediate Similarity NPC162730
0.7395 Intermediate Similarity NPC57994
0.7395 Intermediate Similarity NPC289299
0.7391 Intermediate Similarity NPC64216
0.7384 Intermediate Similarity NPC470785
0.7382 Intermediate Similarity NPC470730
0.7382 Intermediate Similarity NPC477175
0.7373 Intermediate Similarity NPC477549
0.7366 Intermediate Similarity NPC473800
0.7364 Intermediate Similarity NPC473312
0.7362 Intermediate Similarity NPC220852
0.7361 Intermediate Similarity NPC472116
0.736 Intermediate Similarity NPC315467
0.7357 Intermediate Similarity NPC305984
0.7355 Intermediate Similarity NPC471564
0.7354 Intermediate Similarity NPC476116
0.7342 Intermediate Similarity NPC166492
0.7342 Intermediate Similarity NPC473362
0.7339 Intermediate Similarity NPC293917
0.7336 Intermediate Similarity NPC153400
0.7336 Intermediate Similarity NPC272174
0.7333 Intermediate Similarity NPC118940
0.7331 Intermediate Similarity NPC478009
0.7331 Intermediate Similarity NPC478010
0.733 Intermediate Similarity NPC470500
0.733 Intermediate Similarity NPC132539

  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 NPC33949 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
0.8134 Intermediate Similarity NPD4501 Approved
0.8134 Intermediate Similarity NPD4500 Approved
0.8048 Intermediate Similarity NPD4601 Approved
0.8048 Intermediate Similarity NPD4600 Approved
0.7952 Intermediate Similarity NPD53 Approved
0.7952 Intermediate Similarity NPD7778 Approved
0.7952 Intermediate Similarity NPD7777 Approved
0.7926 Intermediate Similarity NPD7470 Discontinued
0.7713 Intermediate Similarity NPD7878 Phase 2
0.7653 Intermediate Similarity NPD5003 Discontinued
0.7545 Intermediate Similarity NPD7666 Phase 3
0.7545 Intermediate Similarity NPD7665 Phase 2
0.7535 Intermediate Similarity NPD7946 Pre-registration
0.7531 Intermediate Similarity NPD8358 Approved
0.7523 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD6770 Approved
0.7478 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD7001 Phase 3
0.7453 Intermediate Similarity NPD4499 Approved
0.7422 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD5426 Phase 3
0.7404 Intermediate Similarity NPD5898 Approved
0.7404 Intermediate Similarity NPD5897 Approved
0.7404 Intermediate Similarity NPD5899 Approved
0.7403 Intermediate Similarity NPD7603 Discontinued
0.7397 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD4602 Approved
0.7387 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD7957 Phase 1
0.7376 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD7791 Approved
0.7362 Intermediate Similarity NPD7952 Approved
0.7362 Intermediate Similarity NPD7790 Approved
0.7362 Intermediate Similarity NPD7953 Approved
0.7362 Intermediate Similarity NPD7789 Approved
0.7362 Intermediate Similarity NPD7950 Approved
0.7362 Intermediate Similarity NPD7951 Approved
0.7358 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD8322 Phase 2
0.7339 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD6999 Discontinued
0.7333 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD5901 Discontinued
0.733 Intermediate Similarity NPD8098 Approved
0.7321 Intermediate Similarity NPD6452 Discontinued
0.7321 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD7944 Discontinued
0.7309 Intermediate Similarity NPD2510 Approved
0.7309 Intermediate Similarity NPD2509 Approved
0.7297 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7731 Approved
0.7296 Intermediate Similarity NPD6977 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6978 Phase 2
0.7296 Intermediate Similarity NPD7730 Approved
0.7294 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD8063 Discontinued
0.7281 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD7688 Phase 1
0.7268 Intermediate Similarity NPD2844 Phase 3
0.7265 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD8093 Discontinued
0.7257 Intermediate Similarity NPD8097 Phase 3
0.7257 Intermediate Similarity NPD8096 Phase 3
0.7253 Intermediate Similarity NPD8289 Discontinued
0.7252 Intermediate Similarity NPD8114 Approved
0.7252 Intermediate Similarity NPD8115 Approved
0.7252 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD5596 Phase 2
0.7251 Intermediate Similarity NPD2094 Phase 2
0.7251 Intermediate Similarity NPD2095 Phase 2
0.7251 Intermediate Similarity NPD2092 Phase 2
0.7243 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD3394 Approved
0.7237 Intermediate Similarity NPD3389 Approved
0.7237 Intermediate Similarity NPD3393 Approved
0.7234 Intermediate Similarity NPD7824 Approved
0.7233 Intermediate Similarity NPD8363 Approved
0.7233 Intermediate Similarity NPD8364 Approved
0.7229 Intermediate Similarity NPD7708 Approved
0.7222 Intermediate Similarity NPD6165 Phase 2
0.7222 Intermediate Similarity NPD6164 Phase 2
0.7217 Intermediate Similarity NPD2096 Phase 2
0.7217 Intermediate Similarity NPD2091 Phase 2
0.721 Intermediate Similarity NPD7271 Approved
0.721 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD2565 Phase 2
0.7209 Intermediate Similarity NPD2564 Approved
0.7207 Intermediate Similarity NPD8072 Approved
0.72 Intermediate Similarity NPD4506 Discontinued
0.7198 Intermediate Similarity NPD6995 Phase 1
0.7196 Intermediate Similarity NPD4948 Discontinued
0.7189 Intermediate Similarity NPD7955 Approved
0.7189 Intermediate Similarity NPD7956 Approved
0.7184 Intermediate Similarity NPD5482 Discontinued
0.7183 Intermediate Similarity NPD7803 Approved
0.7178 Intermediate Similarity NPD7576 Discontinued
0.7176 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD4885 Approved
0.7168 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD6595 Phase 3
0.7143 Intermediate Similarity NPD6665 Discontinued
0.7136 Intermediate Similarity NPD4397 Phase 1
0.7131 Intermediate Similarity NPD8372 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD8325 Phase 3
0.713 Intermediate Similarity NPD8326 Phase 3
0.713 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7781 Approved
0.7119 Intermediate Similarity NPD7780 Approved
0.7103 Intermediate Similarity NPD6227 Discontinued
0.7103 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6263 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7948 Phase 1
0.709 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD7921 Approved
0.7087 Intermediate Similarity NPD8160 Phase 2
0.7085 Intermediate Similarity NPD8073 Approved
0.708 Intermediate Similarity NPD2916 Discontinued
0.7074 Intermediate Similarity NPD8094 Discontinued
0.7062 Intermediate Similarity NPD6642 Approved
0.7062 Intermediate Similarity NPD6641 Approved
0.7054 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD4554 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD8356 Approved
0.7048 Intermediate Similarity NPD5065 Approved
0.7048 Intermediate Similarity NPD482 Approved
0.7045 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD8463 Approved
0.7018 Intermediate Similarity NPD8321 Discontinued
0.7018 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD5913 Phase 3
0.7018 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD2381 Approved
0.7014 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD2380 Approved
0.7014 Intermediate Similarity NPD2382 Approved
0.7012 Intermediate Similarity NPD3006 Discontinued
0.7011 Intermediate Similarity NPD7181 Phase 3
0.7008 Intermediate Similarity NPD6456 Discontinued
0.7004 Intermediate Similarity NPD8430 Approved
0.7 Intermediate Similarity NPD8465 Approved
0.7 Intermediate Similarity NPD43 Approved
0.7 Intermediate Similarity NPD6182 Approved
0.7 Intermediate Similarity NPD8467 Approved
0.7 Intermediate Similarity NPD6183 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD750 Phase 2
0.7 Intermediate Similarity NPD7558 Phase 2
0.7 Intermediate Similarity NPD8466 Approved
0.6996 Remote Similarity NPD484 Approved
0.6996 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6996 Remote Similarity NPD8016 Phase 3
0.6996 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6991 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6986 Remote Similarity NPD1326 Approved
0.6986 Remote Similarity NPD1325 Approved
0.6983 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7865 Approved
0.6974 Remote Similarity NPD4520 Approved
0.697 Remote Similarity NPD7971 Clinical (unspecified phase)
0.697 Remote Similarity NPD7970 Approved
0.6964 Remote Similarity NPD7817 Phase 1
0.6964 Remote Similarity NPD7727 Phase 2
0.6962 Remote Similarity NPD7711 Discontinued
0.6958 Remote Similarity NPD8425 Approved
0.6958 Remote Similarity NPD8426 Approved
0.6949 Remote Similarity NPD7716 Approved
0.6949 Remote Similarity NPD7717 Approved
0.6947 Remote Similarity NPD8272 Phase 2
0.6947 Remote Similarity NPD56 Approved
0.6947 Remote Similarity NPD8282 Approved
0.6947 Remote Similarity NPD8283 Approved
0.6943 Remote Similarity NPD7825 Clinical (unspecified phase)
0.694 Remote Similarity NPD6733 Discontinued
0.6935 Remote Similarity NPD8429 Approved
0.6935 Remote Similarity NPD8427 Approved
0.6935 Remote Similarity NPD8428 Approved
0.6933 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6932 Remote Similarity NPD8246 Approved
0.6932 Remote Similarity NPD8247 Approved
0.6923 Remote Similarity NPD7194 Discontinued
0.6923 Remote Similarity NPD7619 Phase 3
0.6923 Remote Similarity NPD7618 Phase 3
0.6914 Remote Similarity NPD5450 Discontinued
0.6907 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6176 Phase 1
0.6903 Remote Similarity NPD2920 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