NPASS Compound

Structure

NPC475915 OpenBabel07101718292D 21 25 0 0 1 0 0 0 0 0999 V2000 4.5380 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 13 2 0 0 0 0 6 14 2 0 0 0 0 7 15 2 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	276.16
Volume:	300.573
LogP:	3.794
LogD:	3.476
LogS:	-3.687
# Rotatable Bonds:	0
TPSA:	15.27
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	3.391
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.73
MDCK Permeability:	2.0712872355943546e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.537
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.376
30% Bioavailability (F30%):	0.128

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	93.97163391113281%
Volume Distribution (VD):	3.105
Pgp-substrate:	5.728078365325928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.366
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.787
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.987
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	12.963
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.825
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.068
Carcinogencity:	0.601
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC475915

Natural Product ID:	NPC475915
*Common Name:**	(1S)-1,2,3,10,11,12,14,21-Octahydroyohimban
IUPAC Name:	(1S)-1,2,3,10,11,12,14,21-octahydroyohimban
Synonyms:	Demethoxycarbonyl 3,14-Dihydrogambirtannine
Standard InCHIKey:	JJJTUFPBCJFSOI-AVAKVYKDSA-N
Standard InCHI:	InChI=1S/C19H20N2/c1-2-6-14-12-21-10-9-16-15-7-3-4-8-17(15)20-19(16)18(21)11-13(14)5-1/h1-8,16,18-20H,9-12H2/t16?,18-,19?/m0/s1
SMILES:	c1ccc2c(c1)C[C@@H]1N(C2)CCC2C1Nc1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518471
PubChem CID:	44559927
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO15372	Strychnos johnsonii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO15372	Strychnos johnsonii	Species	Loganiaceae	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
IC50	3
Others	3

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11300.0	nM	PMID[456020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12900.0	nM	PMID[456020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18300.0	nM	PMID[456020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	42200.0	nM	PMID[456020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	47400.0	nM	PMID[456020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	89500.0	nM	PMID[456020]

☑ 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 NPC475915 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	807
0.1-0.2	6259
0.2-0.3	17457
0.3-0.4	11404
0.4-0.5	4627
0.5-0.6	1701
0.6-0.7	401
0.7-0.8	35
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8189	Intermediate Similarity	NPC252794
0.8115	Intermediate Similarity	NPC313673
0.8	Intermediate Similarity	NPC291610
0.7815	Intermediate Similarity	NPC79618
0.7801	Intermediate Similarity	NPC109787
0.7788	Intermediate Similarity	NPC329430
0.775	Intermediate Similarity	NPC302790
0.771	Intermediate Similarity	NPC145754
0.7681	Intermediate Similarity	NPC88097
0.7619	Intermediate Similarity	NPC192209
0.7569	Intermediate Similarity	NPC206592
0.7559	Intermediate Similarity	NPC264580
0.7521	Intermediate Similarity	NPC434
0.75	Intermediate Similarity	NPC475990
0.75	Intermediate Similarity	NPC221786
0.75	Intermediate Similarity	NPC474880
0.748	Intermediate Similarity	NPC313449
0.7413	Intermediate Similarity	NPC264589
0.7368	Intermediate Similarity	NPC470926
0.7357	Intermediate Similarity	NPC130251
0.7338	Intermediate Similarity	NPC325252
0.7333	Intermediate Similarity	NPC229173
0.7329	Intermediate Similarity	NPC33421
0.7315	Intermediate Similarity	NPC222029
0.731	Intermediate Similarity	NPC21605
0.7302	Intermediate Similarity	NPC296163
0.7302	Intermediate Similarity	NPC187036
0.7292	Intermediate Similarity	NPC469735
0.7273	Intermediate Similarity	NPC20144
0.7266	Intermediate Similarity	NPC198988
0.7203	Intermediate Similarity	NPC473868
0.7203	Intermediate Similarity	NPC63157
0.7181	Intermediate Similarity	NPC476219
0.7155	Intermediate Similarity	NPC108800
0.7152	Intermediate Similarity	NPC56765
0.7143	Intermediate Similarity	NPC471123
0.7133	Intermediate Similarity	NPC59084
0.7107	Intermediate Similarity	NPC239854
0.7092	Intermediate Similarity	NPC218268
0.708	Intermediate Similarity	NPC258046
0.7063	Intermediate Similarity	NPC186284
0.7063	Intermediate Similarity	NPC22082
0.7063	Intermediate Similarity	NPC301760
0.7059	Intermediate Similarity	NPC469741
0.7059	Intermediate Similarity	NPC478079
0.7059	Intermediate Similarity	NPC476950
0.7055	Intermediate Similarity	NPC204141
0.7054	Intermediate Similarity	NPC288232
0.7051	Intermediate Similarity	NPC474897
0.7039	Intermediate Similarity	NPC276085
0.7034	Intermediate Similarity	NPC311330
0.7014	Intermediate Similarity	NPC2949
0.7013	Intermediate Similarity	NPC21174
0.7013	Intermediate Similarity	NPC271797
0.7007	Intermediate Similarity	NPC469740
0.6983	Remote Similarity	NPC191444
0.698	Remote Similarity	NPC66936
0.698	Remote Similarity	NPC475763
0.6966	Remote Similarity	NPC469537
0.6962	Remote Similarity	NPC242269
0.6957	Remote Similarity	NPC9856
0.6957	Remote Similarity	NPC473417
0.6948	Remote Similarity	NPC85651
0.6928	Remote Similarity	NPC318065
0.6928	Remote Similarity	NPC206819
0.6913	Remote Similarity	NPC473329
0.6903	Remote Similarity	NPC169016
0.6897	Remote Similarity	NPC176858
0.6897	Remote Similarity	NPC115611
0.6887	Remote Similarity	NPC478076
0.6887	Remote Similarity	NPC325903
0.6879	Remote Similarity	NPC316104
0.6879	Remote Similarity	NPC162417
0.6879	Remote Similarity	NPC317430
0.6875	Remote Similarity	NPC280852
0.6867	Remote Similarity	NPC40070
0.6855	Remote Similarity	NPC472123
0.6842	Remote Similarity	NPC476297
0.6842	Remote Similarity	NPC229477
0.6839	Remote Similarity	NPC99632
0.6839	Remote Similarity	NPC282339
0.6824	Remote Similarity	NPC470440
0.6821	Remote Similarity	NPC470233
0.6818	Remote Similarity	NPC41257
0.6815	Remote Similarity	NPC268534
0.6814	Remote Similarity	NPC119677
0.6806	Remote Similarity	NPC469560
0.6772	Remote Similarity	NPC164802
0.6761	Remote Similarity	NPC313352
0.6753	Remote Similarity	NPC286427
0.6738	Remote Similarity	NPC22079
0.6738	Remote Similarity	NPC53044
0.6733	Remote Similarity	NPC469811
0.673	Remote Similarity	NPC472118
0.6727	Remote Similarity	NPC472294
0.6712	Remote Similarity	NPC73767
0.671	Remote Similarity	NPC36495
0.671	Remote Similarity	NPC193410
0.6708	Remote Similarity	NPC475097
0.6691	Remote Similarity	NPC250361
0.669	Remote Similarity	NPC475450
0.6689	Remote Similarity	NPC318086
0.6689	Remote Similarity	NPC321911
0.6688	Remote Similarity	NPC90723
0.6667	Remote Similarity	NPC63545
0.6667	Remote Similarity	NPC474695
0.6667	Remote Similarity	NPC469761
0.6667	Remote Similarity	NPC256288
0.6667	Remote Similarity	NPC81229
0.6667	Remote Similarity	NPC134825
0.6667	Remote Similarity	NPC469780
0.6667	Remote Similarity	NPC284635
0.6667	Remote Similarity	NPC469779
0.6667	Remote Similarity	NPC104070
0.6667	Remote Similarity	NPC469767
0.6667	Remote Similarity	NPC255229
0.6667	Remote Similarity	NPC248117
0.6667	Remote Similarity	NPC472109
0.6667	Remote Similarity	NPC469783
0.6667	Remote Similarity	NPC469768
0.6667	Remote Similarity	NPC469784
0.6667	Remote Similarity	NPC472110
0.6646	Remote Similarity	NPC161861
0.6646	Remote Similarity	NPC2165
0.6646	Remote Similarity	NPC475420
0.6646	Remote Similarity	NPC195507
0.6645	Remote Similarity	NPC243756
0.6645	Remote Similarity	NPC154602
0.6645	Remote Similarity	NPC53947
0.6644	Remote Similarity	NPC243162
0.6643	Remote Similarity	NPC473930
0.6643	Remote Similarity	NPC328590
0.6643	Remote Similarity	NPC209389
0.6627	Remote Similarity	NPC2933
0.6625	Remote Similarity	NPC194411
0.6624	Remote Similarity	NPC194881
0.6624	Remote Similarity	NPC176983
0.6623	Remote Similarity	NPC201380
0.6623	Remote Similarity	NPC477134
0.6623	Remote Similarity	NPC179787
0.6622	Remote Similarity	NPC469766
0.6621	Remote Similarity	NPC96102
0.662	Remote Similarity	NPC475428
0.6619	Remote Similarity	NPC166424
0.6619	Remote Similarity	NPC146373
0.6619	Remote Similarity	NPC245244
0.6603	Remote Similarity	NPC6436
0.6599	Remote Similarity	NPC110126
0.6599	Remote Similarity	NPC471164
0.6599	Remote Similarity	NPC104483
0.6599	Remote Similarity	NPC312092
0.6596	Remote Similarity	NPC473762
0.6594	Remote Similarity	NPC192533
0.6587	Remote Similarity	NPC259626
0.6582	Remote Similarity	NPC317105
0.6577	Remote Similarity	NPC472103
0.6575	Remote Similarity	NPC84911
0.6575	Remote Similarity	NPC105127
0.6575	Remote Similarity	NPC314102
0.6575	Remote Similarity	NPC251722
0.6566	Remote Similarity	NPC470205
0.6566	Remote Similarity	NPC472108
0.6566	Remote Similarity	NPC139291
0.6562	Remote Similarity	NPC63047
0.6562	Remote Similarity	NPC475248
0.6561	Remote Similarity	NPC44773
0.6561	Remote Similarity	NPC215584
0.6561	Remote Similarity	NPC472102
0.6561	Remote Similarity	NPC309531
0.6561	Remote Similarity	NPC68650
0.6556	Remote Similarity	NPC288838
0.6549	Remote Similarity	NPC473587
0.6548	Remote Similarity	NPC473615
0.6547	Remote Similarity	NPC27740
0.6538	Remote Similarity	NPC104345
0.6538	Remote Similarity	NPC216643
0.6538	Remote Similarity	NPC61013
0.6529	Remote Similarity	NPC322040
0.6525	Remote Similarity	NPC30445
0.6525	Remote Similarity	NPC111233
0.6519	Remote Similarity	NPC470203
0.6515	Remote Similarity	NPC314141
0.6509	Remote Similarity	NPC229484
0.6507	Remote Similarity	NPC261195
0.6507	Remote Similarity	NPC29886
0.6503	Remote Similarity	NPC37423
0.6503	Remote Similarity	NPC275305
0.6503	Remote Similarity	NPC282398
0.65	Remote Similarity	NPC472114
0.65	Remote Similarity	NPC279527
0.65	Remote Similarity	NPC214960
0.65	Remote Similarity	NPC472115
0.6496	Remote Similarity	NPC314192
0.6496	Remote Similarity	NPC257490
0.6486	Remote Similarity	NPC470301
0.6478	Remote Similarity	NPC247987
0.6474	Remote Similarity	NPC51054
0.6471	Remote Similarity	NPC226143
0.6471	Remote Similarity	NPC54102
0.6471	Remote Similarity	NPC292675

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 NPC475915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	684
0.2-0.3	1222
0.3-0.4	1560
0.4-0.5	3134
0.5-0.6	1644
0.6-0.7	497
0.7-0.8	67
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8879	High Similarity	NPD5629	Discontinued
0.8632	High Similarity	NPD2914	Approved
0.8632	High Similarity	NPD2913	Approved
0.8462	Intermediate Similarity	NPD2038	Approved
0.8462	Intermediate Similarity	NPD2039	Approved
0.8362	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1950	Approved
0.8333	Intermediate Similarity	NPD1949	Approved
0.8182	Intermediate Similarity	NPD1720	Phase 2
0.8182	Intermediate Similarity	NPD1723	Phase 2
0.8151	Intermediate Similarity	NPD3001	Approved
0.8151	Intermediate Similarity	NPD2999	Approved
0.8136	Intermediate Similarity	NPD4116	Approved
0.7966	Intermediate Similarity	NPD5253	Approved
0.7891	Intermediate Similarity	NPD2940	Approved
0.7891	Intermediate Similarity	NPD2938	Approved
0.7833	Intermediate Similarity	NPD7633	Discontinued
0.7826	Intermediate Similarity	NPD1946	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4114	Approved
0.7815	Intermediate Similarity	NPD4115	Approved
0.7731	Intermediate Similarity	NPD3546	Approved
0.7731	Intermediate Similarity	NPD3545	Approved
0.7727	Intermediate Similarity	NPD3424	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD2467	Approved
0.768	Intermediate Similarity	NPD2463	Approved
0.768	Intermediate Similarity	NPD2464	Approved
0.7643	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD6358	Phase 2
0.7565	Intermediate Similarity	NPD2005	Discontinued
0.7557	Intermediate Similarity	NPD4985	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4734	Approved
0.7542	Intermediate Similarity	NPD4735	Approved
0.754	Intermediate Similarity	NPD6069	Approved
0.754	Intermediate Similarity	NPD6070	Approved
0.748	Intermediate Similarity	NPD7481	Approved
0.748	Intermediate Similarity	NPD7480	Approved
0.7465	Intermediate Similarity	NPD5931	Phase 3
0.7465	Intermediate Similarity	NPD5933	Phase 3
0.7465	Intermediate Similarity	NPD5932	Phase 3
0.7463	Intermediate Similarity	NPD4019	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1916	Discontinued
0.744	Intermediate Similarity	NPD5179	Approved
0.744	Intermediate Similarity	NPD5180	Approved
0.744	Intermediate Similarity	NPD5181	Approved
0.7422	Intermediate Similarity	NPD5657	Phase 3
0.7405	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6548	Approved
0.7391	Intermediate Similarity	NPD6549	Approved
0.7388	Intermediate Similarity	NPD3008	Approved
0.7388	Intermediate Similarity	NPD3011	Approved
0.7388	Intermediate Similarity	NPD3012	Approved
0.7368	Intermediate Similarity	NPD3000	Approved
0.7368	Intermediate Similarity	NPD2997	Approved
0.7368	Intermediate Similarity	NPD2998	Approved
0.7361	Intermediate Similarity	NPD1683	Approved
0.7338	Intermediate Similarity	NPD4411	Phase 1
0.7338	Intermediate Similarity	NPD4410	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5554	Approved
0.7305	Intermediate Similarity	NPD5518	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD993	Approved
0.7295	Intermediate Similarity	NPD990	Approved
0.7293	Intermediate Similarity	NPD2143	Discontinued
0.7273	Intermediate Similarity	NPD5918	Discontinued
0.7244	Intermediate Similarity	NPD5631	Phase 3
0.7239	Intermediate Similarity	NPD6900	Discontinued
0.7236	Intermediate Similarity	NPD6300	Approved
0.7236	Intermediate Similarity	NPD6299	Approved
0.7231	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6342	Discontinued
0.7197	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6498	Approved
0.7143	Intermediate Similarity	NPD6499	Approved
0.7133	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3323	Discontinued
0.7113	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3240	Phase 2
0.7083	Intermediate Similarity	NPD6301	Phase 2
0.7078	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3385	Approved
0.7045	Intermediate Similarity	NPD3957	Phase 2
0.7045	Intermediate Similarity	NPD3955	Approved
0.7045	Intermediate Similarity	NPD3956	Phase 3
0.7015	Intermediate Similarity	NPD7461	Approved
0.7	Intermediate Similarity	NPD3483	Approved
0.7	Intermediate Similarity	NPD3484	Approved
0.6992	Remote Similarity	NPD4546	Discontinued
0.6992	Remote Similarity	NPD4936	Approved
0.6992	Remote Similarity	NPD4937	Approved
0.6991	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5254	Discontinued
0.6984	Remote Similarity	NPD3548	Approved
0.6983	Remote Similarity	NPD5915	Approved
0.6977	Remote Similarity	NPD1813	Discontinued
0.697	Remote Similarity	NPD3498	Approved
0.697	Remote Similarity	NPD3499	Approved
0.697	Remote Similarity	NPD5516	Phase 2
0.697	Remote Similarity	NPD5517	Phase 2
0.6966	Remote Similarity	NPD1722	Approved
0.6957	Remote Similarity	NPD4489	Approved
0.6957	Remote Similarity	NPD4490	Approved
0.6944	Remote Similarity	NPD3625	Discontinued
0.6935	Remote Similarity	NPD233	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8400	Approved
0.6933	Remote Similarity	NPD8402	Approved
0.6933	Remote Similarity	NPD8401	Approved
0.693	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2924	Approved
0.6923	Remote Similarity	NPD2925	Approved
0.6912	Remote Similarity	NPD8128	Discontinued
0.6906	Remote Similarity	NPD6489	Phase 3
0.6897	Remote Similarity	NPD6768	Approved
0.6897	Remote Similarity	NPD6566	Discontinued
0.6894	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4121	Phase 3
0.6887	Remote Similarity	NPD2837	Discontinued
0.6887	Remote Similarity	NPD4120	Approved
0.6884	Remote Similarity	NPD4549	Discontinued
0.6879	Remote Similarity	NPD7200	Approved
0.687	Remote Similarity	NPD4146	Approved
0.687	Remote Similarity	NPD4145	Approved
0.6861	Remote Similarity	NPD572	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2840	Approved
0.6855	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1108	Approved
0.685	Remote Similarity	NPD1107	Approved
0.685	Remote Similarity	NPD1539	Approved
0.6846	Remote Similarity	NPD4085	Approved
0.6846	Remote Similarity	NPD3551	Approved
0.6842	Remote Similarity	NPD5743	Approved
0.6842	Remote Similarity	NPD5741	Approved
0.6842	Remote Similarity	NPD5742	Approved
0.6842	Remote Similarity	NPD1922	Discontinued
0.6835	Remote Similarity	NPD8263	Discontinued
0.6835	Remote Similarity	NPD4365	Phase 2
0.6833	Remote Similarity	NPD5963	Phase 2
0.6833	Remote Similarity	NPD5964	Phase 2
0.6832	Remote Similarity	NPD4181	Approved
0.6831	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7099	Approved
0.6792	Remote Similarity	NPD3609	Approved
0.6792	Remote Similarity	NPD3610	Approved
0.6791	Remote Similarity	NPD2340	Discontinued
0.6788	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1937	Approved
0.6786	Remote Similarity	NPD5782	Phase 3
0.678	Remote Similarity	NPD4543	Discontinued
0.6772	Remote Similarity	NPD477	Phase 1
0.6769	Remote Similarity	NPD6562	Approved
0.6769	Remote Similarity	NPD6561	Approved
0.6767	Remote Similarity	NPD3954	Approved
0.6757	Remote Similarity	NPD7017	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2538	Approved
0.6754	Remote Similarity	NPD2539	Approved
0.6754	Remote Similarity	NPD5178	Approved
0.6752	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1064	Approved
0.6746	Remote Similarity	NPD1065	Approved
0.6744	Remote Similarity	NPD2521	Approved
0.6744	Remote Similarity	NPD3566	Approved
0.6744	Remote Similarity	NPD2519	Approved
0.6744	Remote Similarity	NPD3036	Approved
0.6744	Remote Similarity	NPD2518	Approved
0.6744	Remote Similarity	NPD3565	Approved
0.6735	Remote Similarity	NPD5024	Approved
0.6735	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5526	Phase 2
0.6732	Remote Similarity	NPD976	Approved
0.6732	Remote Similarity	NPD977	Approved
0.6732	Remote Similarity	NPD975	Approved
0.6724	Remote Similarity	NPD3426	Approved
0.6724	Remote Similarity	NPD3428	Approved
0.6723	Remote Similarity	NPD4408	Approved
0.6723	Remote Similarity	NPD4407	Approved
0.6723	Remote Similarity	NPD4405	Approved
0.672	Remote Similarity	NPD2939	Approved
0.672	Remote Similarity	NPD2937	Phase 1
0.6713	Remote Similarity	NPD3944	Approved
0.6713	Remote Similarity	NPD3942	Approved
0.6712	Remote Similarity	NPD786	Approved
0.6712	Remote Similarity	NPD2010	Phase 3
0.6693	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5130	Phase 3
0.6692	Remote Similarity	NPD299	Phase 3
0.669	Remote Similarity	NPD7254	Discontinued
0.6689	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2866	Approved
0.6688	Remote Similarity	NPD2150	Discontinued
0.6667	Remote Similarity	NPD2878	Approved
0.6667	Remote Similarity	NPD6892	Discontinued
0.6667	Remote Similarity	NPD3980	Approved
0.6667	Remote Similarity	NPD3982	Approved
0.6667	Remote Similarity	NPD735	Approved
0.6667	Remote Similarity	NPD736	Approved
0.6667	Remote Similarity	NPD3654	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data