NPASS Compound

Structure

CID267408 OpenBabel06191716072D 22 26 0 0 1 0 0 0 0 0999 V2000 -3.3314 -3.6405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6128 0.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4097 0.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8038 0.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3974 -0.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1968 -3.6574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9901 -4.1146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6041 -2.2703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9116 0.0958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1920 -2.7322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7915 -0.8872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5884 -1.3613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6032 -1.3549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9858 -2.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9930 -1.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7938 -2.7353 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5924 -2.2743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1906 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7839 -3.6563 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3840 -2.7290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2844 -0.7415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 2 0 0 0 0 5 12 2 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 15 18 1 0 0 0 0 16 14 1 6 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.12
Volume:	298.651
LogP:	2.391
LogD:	2.692
LogS:	-2.364
# Rotatable Bonds:	1
TPSA:	39.72
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.878
Synthetic Accessibility Score:	3.591
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847
MDCK Permeability:	2.729833977355156e-05
Pgp-inhibitor:	0.449
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	90.6733169555664%
Volume Distribution (VD):	2.278
Pgp-substrate:	3.1166558265686035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.72
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.385
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.448
CYP2D6-inhibitor:	0.938
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.611

ADMET: Excretion

Clearance (CL):	11.32
Half-life (T1/2):	0.055

ADMET: Toxicity

hERG Blockers:	0.433
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.327
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.739
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.197
Carcinogencity:	0.617
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC267408

Natural Product ID:	NPC267408
*Common Name:**	Pachypodantine
IUPAC Name:	n.a.
Synonyms:	Pachypodantine
Standard InCHIKey:	OBJBIHSGZLMMBX-IRXDYDNUSA-N
Standard InCHI:	InChI=1S/C18H17NO3/c1-20-17-12-5-3-2-4-11(12)15-14-10(6-7-19-16(14)17)8-13-18(15)22-9-21-13/h2-5,8,16-17,19H,6-7,9H2,1H3/t16-,17-/m0/s1
SMILES:	CO[C@H]1c2ccccc2c2c3[C@@H]1NCCc3cc1c2OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523036
PubChem CID:	44566390
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620236]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21816	Calea jamaicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25164	Polyalthia suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24593	Campanula pyramidalis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25009	Cystoseira myrica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24939	Veronica officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13718	Poria tenuis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12599.1	Pinus leiophylla var. chihuahuana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24123	Ramalina scopulorum	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28729	Spirostachys africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24723	Ophiorrhiza bracteata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	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

Activity Type	# Activity
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	25000.0	nM	PMID[476507]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MTC	=	20.0	uM	PMID[476507]

☑ 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 NPC267408 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1947
0.2-0.3	9327
0.3-0.4	8629
0.4-0.5	8422
0.5-0.6	11129
0.6-0.7	2108
0.7-0.8	576
0.8-0.85	87
0.85-0.9	44
0.9-0.95	37
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC476575
0.9509	High Similarity	NPC6152
0.9444	High Similarity	NPC86144
0.9444	High Similarity	NPC304659
0.9321	High Similarity	NPC189470
0.9286	High Similarity	NPC126284
0.9281	High Similarity	NPC112575
0.9264	High Similarity	NPC225774
0.9249	High Similarity	NPC117717
0.9235	High Similarity	NPC156576
0.9231	High Similarity	NPC474506
0.9231	High Similarity	NPC32413
0.9226	High Similarity	NPC23219
0.9222	High Similarity	NPC477558
0.9207	High Similarity	NPC476432
0.9207	High Similarity	NPC219341
0.9207	High Similarity	NPC24264
0.9176	High Similarity	NPC248642
0.9172	High Similarity	NPC470879
0.9172	High Similarity	NPC258695
0.9152	High Similarity	NPC247389
0.9146	High Similarity	NPC302527
0.9146	High Similarity	NPC16805
0.9146	High Similarity	NPC167546
0.9123	High Similarity	NPC135772
0.9118	High Similarity	NPC312918
0.9118	High Similarity	NPC155442
0.9118	High Similarity	NPC476574
0.9118	High Similarity	NPC477561
0.908	High Similarity	NPC477559
0.908	High Similarity	NPC266753
0.908	High Similarity	NPC160298
0.908	High Similarity	NPC232924
0.908	High Similarity	NPC306902
0.9075	High Similarity	NPC237579
0.9042	High Similarity	NPC152212
0.9036	High Similarity	NPC210918
0.9012	High Similarity	NPC203784
0.9012	High Similarity	NPC170503
0.9012	High Similarity	NPC126519
0.8953	High Similarity	NPC275132
0.8908	High Similarity	NPC214116
0.8908	High Similarity	NPC57036
0.8876	High Similarity	NPC149090
0.8876	High Similarity	NPC19520
0.8864	High Similarity	NPC475754
0.8857	High Similarity	NPC476576
0.8857	High Similarity	NPC186546
0.881	High Similarity	NPC204947
0.881	High Similarity	NPC298979
0.8779	High Similarity	NPC114364
0.8779	High Similarity	NPC320223
0.8772	High Similarity	NPC128560
0.8772	High Similarity	NPC229166
0.8772	High Similarity	NPC199465
0.8757	High Similarity	NPC241055
0.8728	High Similarity	NPC220961
0.8727	High Similarity	NPC476572
0.872	High Similarity	NPC99659
0.872	High Similarity	NPC325871
0.8713	High Similarity	NPC66341
0.8713	High Similarity	NPC192135
0.8713	High Similarity	NPC477020
0.8706	High Similarity	NPC26240
0.8706	High Similarity	NPC69712
0.8706	High Similarity	NPC477562
0.869	High Similarity	NPC168409
0.8671	High Similarity	NPC294790
0.8671	High Similarity	NPC148693
0.8671	High Similarity	NPC118633
0.865	High Similarity	NPC81733
0.865	High Similarity	NPC326316
0.8639	High Similarity	NPC35627
0.8639	High Similarity	NPC476573
0.8639	High Similarity	NPC81247
0.8523	High Similarity	NPC116284
0.8514	High Similarity	NPC474507
0.8506	High Similarity	NPC476577
0.8506	High Similarity	NPC173416
0.8506	High Similarity	NPC148709
0.8497	Intermediate Similarity	NPC2314
0.8418	Intermediate Similarity	NPC233718
0.8383	Intermediate Similarity	NPC216459
0.8383	Intermediate Similarity	NPC138487
0.8383	Intermediate Similarity	NPC244112
0.8383	Intermediate Similarity	NPC41178
0.8372	Intermediate Similarity	NPC158376
0.8372	Intermediate Similarity	NPC145832
0.8372	Intermediate Similarity	NPC81218
0.8372	Intermediate Similarity	NPC117188
0.8372	Intermediate Similarity	NPC205421
0.8372	Intermediate Similarity	NPC474931
0.8372	Intermediate Similarity	NPC12053
0.8372	Intermediate Similarity	NPC150879
0.8372	Intermediate Similarity	NPC306555
0.8363	Intermediate Similarity	NPC306843
0.8363	Intermediate Similarity	NPC477563
0.8363	Intermediate Similarity	NPC196447
0.8363	Intermediate Similarity	NPC78222
0.8363	Intermediate Similarity	NPC136508
0.8363	Intermediate Similarity	NPC96603
0.8363	Intermediate Similarity	NPC13504
0.8363	Intermediate Similarity	NPC212794
0.8363	Intermediate Similarity	NPC253043
0.8354	Intermediate Similarity	NPC475959
0.8343	Intermediate Similarity	NPC477080
0.8333	Intermediate Similarity	NPC146288
0.8304	Intermediate Similarity	NPC324144
0.8304	Intermediate Similarity	NPC1229
0.8294	Intermediate Similarity	NPC166014
0.8294	Intermediate Similarity	NPC27410
0.8287	Intermediate Similarity	NPC82763
0.8274	Intermediate Similarity	NPC76079
0.8256	Intermediate Similarity	NPC247972
0.8245	Intermediate Similarity	NPC244606
0.8245	Intermediate Similarity	NPC156728
0.8232	Intermediate Similarity	NPC312531
0.8225	Intermediate Similarity	NPC323443
0.8225	Intermediate Similarity	NPC234392
0.8225	Intermediate Similarity	NPC31311
0.8225	Intermediate Similarity	NPC180756
0.8198	Intermediate Similarity	NPC233650
0.8193	Intermediate Similarity	NPC219162
0.8193	Intermediate Similarity	NPC211296
0.8187	Intermediate Similarity	NPC281581
0.8172	Intermediate Similarity	NPC212163
0.8171	Intermediate Similarity	NPC168753
0.8171	Intermediate Similarity	NPC118274
0.8168	Intermediate Similarity	NPC46990
0.8156	Intermediate Similarity	NPC179704
0.8155	Intermediate Similarity	NPC233029
0.8155	Intermediate Similarity	NPC210148
0.815	Intermediate Similarity	NPC134858
0.8136	Intermediate Similarity	NPC329969
0.8129	Intermediate Similarity	NPC7393
0.8125	Intermediate Similarity	NPC239775
0.8114	Intermediate Similarity	NPC82533
0.8114	Intermediate Similarity	NPC290759
0.8114	Intermediate Similarity	NPC266176
0.8114	Intermediate Similarity	NPC158148
0.8111	Intermediate Similarity	NPC249405
0.8092	Intermediate Similarity	NPC320104
0.809	Intermediate Similarity	NPC287588
0.8085	Intermediate Similarity	NPC295676
0.8084	Intermediate Similarity	NPC60538
0.8084	Intermediate Similarity	NPC207824
0.8072	Intermediate Similarity	NPC90844
0.8072	Intermediate Similarity	NPC95075
0.8072	Intermediate Similarity	NPC253883
0.8068	Intermediate Similarity	NPC75958
0.8061	Intermediate Similarity	NPC145304
0.8059	Intermediate Similarity	NPC93593
0.8059	Intermediate Similarity	NPC78733
0.8057	Intermediate Similarity	NPC57812
0.8057	Intermediate Similarity	NPC210140
0.8057	Intermediate Similarity	NPC474324
0.8047	Intermediate Similarity	NPC148898
0.8046	Intermediate Similarity	NPC238530
0.8046	Intermediate Similarity	NPC169743
0.8046	Intermediate Similarity	NPC232514
0.8046	Intermediate Similarity	NPC276944
0.8037	Intermediate Similarity	NPC470925
0.8033	Intermediate Similarity	NPC474904
0.8024	Intermediate Similarity	NPC130941
0.8023	Intermediate Similarity	NPC65403
0.8023	Intermediate Similarity	NPC477640
0.8023	Intermediate Similarity	NPC225597
0.8023	Intermediate Similarity	NPC470739
0.8011	Intermediate Similarity	NPC58766
0.8011	Intermediate Similarity	NPC475686
0.8011	Intermediate Similarity	NPC475845
0.8	Intermediate Similarity	NPC477564
0.8	Intermediate Similarity	NPC2295
0.8	Intermediate Similarity	NPC244554
0.7988	Intermediate Similarity	NPC76213
0.7988	Intermediate Similarity	NPC277669
0.7976	Intermediate Similarity	NPC92541
0.7975	Intermediate Similarity	NPC314682
0.7966	Intermediate Similarity	NPC474708
0.7966	Intermediate Similarity	NPC311991
0.7966	Intermediate Similarity	NPC474475
0.7964	Intermediate Similarity	NPC106295
0.7964	Intermediate Similarity	NPC51957
0.7964	Intermediate Similarity	NPC210437
0.7964	Intermediate Similarity	NPC16107
0.7964	Intermediate Similarity	NPC476144
0.7963	Intermediate Similarity	NPC253429
0.7955	Intermediate Similarity	NPC190332
0.7955	Intermediate Similarity	NPC181653
0.7941	Intermediate Similarity	NPC470924
0.7941	Intermediate Similarity	NPC114124
0.7933	Intermediate Similarity	NPC187678
0.7931	Intermediate Similarity	NPC60186
0.7927	Intermediate Similarity	NPC328750
0.7927	Intermediate Similarity	NPC188163
0.7927	Intermediate Similarity	NPC213206
0.7927	Intermediate Similarity	NPC474915
0.7919	Intermediate Similarity	NPC111485
0.7917	Intermediate Similarity	NPC7467
0.7912	Intermediate Similarity	NPC73492

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 NPC267408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	761
0.2-0.3	1120
0.3-0.4	2149
0.4-0.5	2694
0.5-0.6	1519
0.6-0.7	573
0.7-0.8	113
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8103	Intermediate Similarity	NPD3051	Approved
0.8061	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD4481	Phase 3
0.7976	Intermediate Similarity	NPD5976	Discontinued
0.7976	Intermediate Similarity	NPD4727	Phase 1
0.7964	Intermediate Similarity	NPD4584	Approved
0.7955	Intermediate Similarity	NPD2970	Approved
0.7955	Intermediate Similarity	NPD2969	Approved
0.7927	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD2977	Approved
0.7907	Intermediate Similarity	NPD2978	Approved
0.788	Intermediate Similarity	NPD7906	Approved
0.787	Intermediate Similarity	NPD6030	Approved
0.787	Intermediate Similarity	NPD6031	Approved
0.7857	Intermediate Similarity	NPD4578	Approved
0.7857	Intermediate Similarity	NPD4577	Approved
0.7849	Intermediate Similarity	NPD7298	Approved
0.7809	Intermediate Similarity	NPD2489	Approved
0.7809	Intermediate Similarity	NPD27	Approved
0.7784	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4420	Approved
0.773	Intermediate Similarity	NPD4663	Approved
0.7714	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5241	Discontinued
0.7663	Intermediate Similarity	NPD2968	Approved
0.7663	Intermediate Similarity	NPD2971	Approved
0.7654	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6107	Approved
0.7588	Intermediate Similarity	NPD2420	Approved
0.7588	Intermediate Similarity	NPD2421	Approved
0.7584	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8156	Discontinued
0.7577	Intermediate Similarity	NPD5005	Approved
0.7577	Intermediate Similarity	NPD5006	Approved
0.7529	Intermediate Similarity	NPD3845	Phase 1
0.7529	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8252	Approved
0.7527	Intermediate Similarity	NPD8099	Discontinued
0.7527	Intermediate Similarity	NPD8251	Approved
0.7514	Intermediate Similarity	NPD6788	Approved
0.75	Intermediate Similarity	NPD2973	Approved
0.75	Intermediate Similarity	NPD2975	Approved
0.75	Intermediate Similarity	NPD2974	Approved
0.7473	Intermediate Similarity	NPD7310	Approved
0.7473	Intermediate Similarity	NPD7312	Approved
0.7473	Intermediate Similarity	NPD7313	Approved
0.7473	Intermediate Similarity	NPD7311	Approved
0.7471	Intermediate Similarity	NPD5160	Discontinued
0.7471	Intermediate Similarity	NPD4017	Approved
0.7456	Intermediate Similarity	NPD3060	Approved
0.7442	Intermediate Similarity	NPD1424	Approved
0.7433	Intermediate Similarity	NPD6851	Approved
0.7433	Intermediate Similarity	NPD7309	Approved
0.7433	Intermediate Similarity	NPD6853	Approved
0.743	Intermediate Similarity	NPD7400	Phase 3
0.7413	Intermediate Similarity	NPD7827	Phase 1
0.7405	Intermediate Similarity	NPD6297	Approved
0.7403	Intermediate Similarity	NPD6071	Discontinued
0.7399	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6042	Phase 2
0.7391	Intermediate Similarity	NPD42	Phase 2
0.7385	Intermediate Similarity	NPD4580	Approved
0.7368	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2563	Approved
0.736	Intermediate Similarity	NPD2560	Approved
0.7347	Intermediate Similarity	NPD3450	Approved
0.7347	Intermediate Similarity	NPD2494	Approved
0.7347	Intermediate Similarity	NPD2493	Approved
0.7347	Intermediate Similarity	NPD3452	Approved
0.7333	Intermediate Similarity	NPD5709	Phase 3
0.733	Intermediate Similarity	NPD2490	Approved
0.733	Intermediate Similarity	NPD2488	Approved
0.7326	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4166	Phase 2
0.73	Intermediate Similarity	NPD4859	Phase 1
0.7294	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4666	Phase 3
0.7289	Intermediate Similarity	NPD3109	Approved
0.7289	Intermediate Similarity	NPD3110	Approved
0.7288	Intermediate Similarity	NPD4772	Phase 2
0.7288	Intermediate Similarity	NPD4773	Phase 2
0.7283	Intermediate Similarity	NPD7598	Phase 2
0.7278	Intermediate Similarity	NPD7833	Phase 2
0.7278	Intermediate Similarity	NPD7831	Phase 2
0.7278	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3639	Approved
0.7257	Intermediate Similarity	NPD3640	Phase 3
0.7257	Intermediate Similarity	NPD3641	Approved
0.7251	Intermediate Similarity	NPD4162	Approved
0.7251	Intermediate Similarity	NPD4236	Phase 3
0.7251	Intermediate Similarity	NPD4237	Approved
0.7249	Intermediate Similarity	NPD8054	Approved
0.7249	Intermediate Similarity	NPD8053	Approved
0.7247	Intermediate Similarity	NPD3383	Approved
0.7247	Intermediate Similarity	NPD3384	Approved
0.7247	Intermediate Similarity	NPD3382	Approved
0.7236	Intermediate Similarity	NPD4583	Approved
0.7236	Intermediate Similarity	NPD4582	Approved
0.7229	Intermediate Similarity	NPD3530	Approved
0.7229	Intermediate Similarity	NPD3532	Approved
0.7229	Intermediate Similarity	NPD3531	Approved
0.7228	Intermediate Similarity	NPD2898	Approved
0.7208	Intermediate Similarity	NPD5457	Discontinued
0.72	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6037	Discontinued
0.7186	Intermediate Similarity	NPD4002	Approved
0.7186	Intermediate Similarity	NPD4004	Approved
0.7157	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7047	Phase 3
0.7135	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2154	Approved
0.7118	Intermediate Similarity	NPD2155	Approved
0.7118	Intermediate Similarity	NPD2156	Approved
0.7118	Intermediate Similarity	NPD1753	Discontinued
0.711	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5754	Discontinued
0.7108	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD2845	Phase 2
0.7098	Intermediate Similarity	NPD2843	Phase 2
0.7095	Intermediate Similarity	NPD6997	Phase 2
0.7092	Intermediate Similarity	NPD5582	Discontinued
0.7079	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2677	Approved
0.7066	Intermediate Similarity	NPD5718	Phase 2
0.7066	Intermediate Similarity	NPD1336	Approved
0.7065	Intermediate Similarity	NPD4040	Phase 1
0.7047	Intermediate Similarity	NPD3349	Phase 2
0.7045	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4107	Approved
0.7024	Intermediate Similarity	NPD4474	Approved
0.7024	Intermediate Similarity	NPD4475	Approved
0.7022	Intermediate Similarity	NPD4210	Discontinued
0.7017	Intermediate Similarity	NPD4585	Approved
0.6995	Remote Similarity	NPD5604	Discontinued
0.6995	Remote Similarity	NPD4055	Discovery
0.6994	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6688	Approved
0.6989	Remote Similarity	NPD6687	Approved
0.6977	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7802	Discontinued
0.6961	Remote Similarity	NPD5720	Discontinued
0.6959	Remote Similarity	NPD6625	Approved
0.6959	Remote Similarity	NPD6723	Discontinued
0.6949	Remote Similarity	NPD2874	Phase 2
0.6946	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4010	Discontinued
0.6932	Remote Similarity	NPD3122	Phase 3
0.6931	Remote Similarity	NPD5095	Phase 3
0.6931	Remote Similarity	NPD5096	Phase 3
0.6927	Remote Similarity	NPD3687	Approved
0.6927	Remote Similarity	NPD3686	Approved
0.6923	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5677	Discontinued
0.6915	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4482	Phase 3
0.6911	Remote Similarity	NPD7039	Approved
0.6911	Remote Similarity	NPD7038	Approved
0.6906	Remote Similarity	NPD1757	Discontinued
0.6904	Remote Similarity	NPD7262	Phase 1
0.6902	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD817	Approved
0.6901	Remote Similarity	NPD3054	Approved
0.6901	Remote Similarity	NPD823	Approved
0.6901	Remote Similarity	NPD3052	Approved
0.6895	Remote Similarity	NPD3885	Approved
0.6893	Remote Similarity	NPD3124	Discontinued
0.6893	Remote Similarity	NPD1774	Approved
0.6881	Remote Similarity	NPD3057	Approved
0.6872	Remote Similarity	NPD3763	Approved
0.6868	Remote Similarity	NPD5722	Discontinued
0.6863	Remote Similarity	NPD7999	Approved
0.6858	Remote Similarity	NPD8153	Approved
0.6858	Remote Similarity	NPD8152	Approved
0.6857	Remote Similarity	NPD5177	Phase 3
0.6842	Remote Similarity	NPD1341	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5312	Approved
0.6842	Remote Similarity	NPD4873	Discontinued
0.6842	Remote Similarity	NPD5313	Approved
0.6842	Remote Similarity	NPD3933	Discontinued
0.6839	Remote Similarity	NPD4725	Approved
0.6839	Remote Similarity	NPD1375	Discontinued
0.6839	Remote Similarity	NPD7281	Phase 3
0.6839	Remote Similarity	NPD7280	Phase 3
0.6839	Remote Similarity	NPD4721	Approved
0.6839	Remote Similarity	NPD4726	Approved
0.6839	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5938	Phase 3
0.6821	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4108	Discontinued
0.6818	Remote Similarity	NPD7466	Approved
0.6818	Remote Similarity	NPD6748	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