NPASS Compound

Structure

NPC476379 OpenBabel07101718192D 25 28 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 12 17 1 1 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 6 0 0 0 14 25 1 0 0 0 0 15 19 1 6 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 3 1 1 0 0 0 18 4 1 1 0 0 0 19 24 1 1 0 0 0 20 11 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	361.565
LogP:	2.508
LogD:	0.963
LogS:	-3.552
# Rotatable Bonds:	2
TPSA:	90.29
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	4.979
Fsp3:	0.95
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:	-5.411
MDCK Permeability:	1.5663663361920044e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.505

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.408
Plasma Protein Binding (PPB):	83.04593658447266%
Volume Distribution (VD):	0.534
Pgp-substrate:	21.146072387695312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	1.747
Half-life (T1/2):	0.617

ADMET: Toxicity

hERG Blockers:	0.264
Human Hepatotoxicity (H-HT):	0.876
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.353
Carcinogencity:	0.058
Eye Corrosion:	0.022
Eye Irritation:	0.075
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC476379

Natural Product ID:	NPC476379
*Common Name:**	Abiesadine C
IUPAC Name:	n.a.
Synonyms:	Abiesadine C
Standard InCHIKey:	VUKHORQAZYZECW-BOOJXVHTSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-11(2)20-14(25-20)10-13-17(3)7-5-8-18(4,16(22)23)12(17)6-9-19(13,24)15(20)21/h11-15,21,24H,5-10H2,1-4H3,(H,22,23)/t12-,13?,14+,15-,17+,18-,19+,20+/m1/s1
SMILES:	CC(C)C12C(O1)CC3C4(CCCC(C4CCC3(C2O)O)(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590316
PubChem CID:	46230019
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[448242]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[448242]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[448242]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[448242]

☑ 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 NPC476379 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	496
0.1-0.2	3287
0.2-0.3	7444
0.3-0.4	14749
0.4-0.5	6677
0.5-0.6	5241
0.6-0.7	4051
0.7-0.8	717
0.8-0.85	28
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8791	High Similarity	NPC235109
0.8681	High Similarity	NPC82633
0.8652	High Similarity	NPC470114
0.8636	High Similarity	NPC476435
0.8588	High Similarity	NPC477446
0.8588	High Similarity	NPC470155
0.8588	High Similarity	NPC477447
0.8587	High Similarity	NPC163685
0.8571	High Similarity	NPC472951
0.8571	High Similarity	NPC472943
0.8471	Intermediate Similarity	NPC470156
0.8471	Intermediate Similarity	NPC470154
0.8444	Intermediate Similarity	NPC50443
0.8444	Intermediate Similarity	NPC18536
0.8427	Intermediate Similarity	NPC471221
0.8409	Intermediate Similarity	NPC235196
0.8409	Intermediate Similarity	NPC228593
0.8409	Intermediate Similarity	NPC474215
0.8409	Intermediate Similarity	NPC475729
0.8391	Intermediate Similarity	NPC473299
0.8387	Intermediate Similarity	NPC116683
0.8372	Intermediate Similarity	NPC202688
0.8372	Intermediate Similarity	NPC154043
0.8372	Intermediate Similarity	NPC60018
0.8372	Intermediate Similarity	NPC121121
0.837	Intermediate Similarity	NPC477495
0.8315	Intermediate Similarity	NPC202937
0.8295	Intermediate Similarity	NPC131350
0.8295	Intermediate Similarity	NPC266651
0.8276	Intermediate Similarity	NPC227170
0.8276	Intermediate Similarity	NPC269684
0.8261	Intermediate Similarity	NPC475307
0.8242	Intermediate Similarity	NPC185529
0.8242	Intermediate Similarity	NPC472146
0.8211	Intermediate Similarity	NPC472144
0.8202	Intermediate Similarity	NPC155531
0.8202	Intermediate Similarity	NPC215968
0.8202	Intermediate Similarity	NPC83242
0.8191	Intermediate Similarity	NPC475785
0.8191	Intermediate Similarity	NPC477264
0.814	Intermediate Similarity	NPC16449
0.8132	Intermediate Similarity	NPC56962
0.8132	Intermediate Similarity	NPC24705
0.8111	Intermediate Similarity	NPC62202
0.8111	Intermediate Similarity	NPC45833
0.8111	Intermediate Similarity	NPC110365
0.8111	Intermediate Similarity	NPC470920
0.8111	Intermediate Similarity	NPC213658
0.8105	Intermediate Similarity	NPC472145
0.809	Intermediate Similarity	NPC477445
0.8085	Intermediate Similarity	NPC17336
0.8068	Intermediate Similarity	NPC259173
0.8046	Intermediate Similarity	NPC211049
0.8046	Intermediate Similarity	NPC475743
0.8046	Intermediate Similarity	NPC12933
0.8023	Intermediate Similarity	NPC80891
0.8023	Intermediate Similarity	NPC201276
0.8	Intermediate Similarity	NPC307865
0.8	Intermediate Similarity	NPC471410
0.8	Intermediate Similarity	NPC477283
0.8	Intermediate Similarity	NPC475765
0.8	Intermediate Similarity	NPC472272
0.8	Intermediate Similarity	NPC471411
0.8	Intermediate Similarity	NPC472745
0.7978	Intermediate Similarity	NPC65133
0.7978	Intermediate Similarity	NPC219535
0.7978	Intermediate Similarity	NPC473336
0.7978	Intermediate Similarity	NPC477434
0.7978	Intermediate Similarity	NPC471044
0.7978	Intermediate Similarity	NPC237938
0.7976	Intermediate Similarity	NPC472950
0.7976	Intermediate Similarity	NPC472952
0.7961	Intermediate Similarity	NPC477489
0.7959	Intermediate Similarity	NPC471254
0.7938	Intermediate Similarity	NPC477655
0.7938	Intermediate Similarity	NPC477656
0.7935	Intermediate Similarity	NPC477440
0.7935	Intermediate Similarity	NPC477443
0.7931	Intermediate Similarity	NPC186594
0.7917	Intermediate Similarity	NPC471241
0.7917	Intermediate Similarity	NPC266417
0.7917	Intermediate Similarity	NPC472273
0.7912	Intermediate Similarity	NPC263802
0.7912	Intermediate Similarity	NPC239938
0.7912	Intermediate Similarity	NPC5943
0.7907	Intermediate Similarity	NPC324700
0.7907	Intermediate Similarity	NPC34046
0.7907	Intermediate Similarity	NPC80089
0.7907	Intermediate Similarity	NPC224802
0.7907	Intermediate Similarity	NPC191345
0.7907	Intermediate Similarity	NPC171426
0.7907	Intermediate Similarity	NPC252483
0.79	Intermediate Similarity	NPC477877
0.7889	Intermediate Similarity	NPC477205
0.7889	Intermediate Similarity	NPC476715
0.7879	Intermediate Similarity	NPC34562
0.7872	Intermediate Similarity	NPC474379
0.7865	Intermediate Similarity	NPC111582
0.7865	Intermediate Similarity	NPC477285
0.7865	Intermediate Similarity	NPC241959
0.7865	Intermediate Similarity	NPC15091
0.7857	Intermediate Similarity	NPC470151
0.7849	Intermediate Similarity	NPC77756
0.7849	Intermediate Similarity	NPC477442
0.7849	Intermediate Similarity	NPC477433
0.7849	Intermediate Similarity	NPC477444
0.7843	Intermediate Similarity	NPC299590
0.7843	Intermediate Similarity	NPC154906
0.7841	Intermediate Similarity	NPC116320
0.7841	Intermediate Similarity	NPC476071
0.7841	Intermediate Similarity	NPC119922
0.7826	Intermediate Similarity	NPC226491
0.7826	Intermediate Similarity	NPC477614
0.7826	Intermediate Similarity	NPC470872
0.7812	Intermediate Similarity	NPC256227
0.7805	Intermediate Similarity	NPC470833
0.7802	Intermediate Similarity	NPC131365
0.7802	Intermediate Similarity	NPC302111
0.7802	Intermediate Similarity	NPC80700
0.78	Intermediate Similarity	NPC100078
0.78	Intermediate Similarity	NPC301787
0.7791	Intermediate Similarity	NPC317913
0.7791	Intermediate Similarity	NPC207010
0.7789	Intermediate Similarity	NPC470423
0.7778	Intermediate Similarity	NPC18953
0.7766	Intermediate Similarity	NPC216137
0.7766	Intermediate Similarity	NPC219516
0.7766	Intermediate Similarity	NPC52756
0.7766	Intermediate Similarity	NPC475878
0.7766	Intermediate Similarity	NPC473066
0.7753	Intermediate Similarity	NPC100366
0.7753	Intermediate Similarity	NPC242771
0.7753	Intermediate Similarity	NPC311642
0.7753	Intermediate Similarity	NPC477286
0.7753	Intermediate Similarity	NPC216800
0.7753	Intermediate Similarity	NPC286719
0.7753	Intermediate Similarity	NPC164289
0.7745	Intermediate Similarity	NPC208461
0.7745	Intermediate Similarity	NPC289702
0.7742	Intermediate Similarity	NPC67653
0.7742	Intermediate Similarity	NPC471459
0.7727	Intermediate Similarity	NPC186588
0.7727	Intermediate Similarity	NPC125366
0.7723	Intermediate Similarity	NPC166079
0.7723	Intermediate Similarity	NPC470587
0.7723	Intermediate Similarity	NPC222833
0.7714	Intermediate Similarity	NPC97002
0.7708	Intermediate Similarity	NPC215570
0.7708	Intermediate Similarity	NPC62407
0.7708	Intermediate Similarity	NPC470031
0.7708	Intermediate Similarity	NPC287354
0.7701	Intermediate Similarity	NPC31031
0.7701	Intermediate Similarity	NPC43463
0.7701	Intermediate Similarity	NPC472608
0.7701	Intermediate Similarity	NPC147993
0.7701	Intermediate Similarity	NPC243594
0.77	Intermediate Similarity	NPC225238
0.77	Intermediate Similarity	NPC473406
0.77	Intermediate Similarity	NPC61442
0.77	Intermediate Similarity	NPC471253
0.7684	Intermediate Similarity	NPC256104
0.7684	Intermediate Similarity	NPC476189
0.7684	Intermediate Similarity	NPC211845
0.7684	Intermediate Similarity	NPC182740
0.7684	Intermediate Similarity	NPC122083
0.7677	Intermediate Similarity	NPC98225
0.7674	Intermediate Similarity	NPC4209
0.7674	Intermediate Similarity	NPC474020
0.7674	Intermediate Similarity	NPC136424
0.7667	Intermediate Similarity	NPC472744
0.766	Intermediate Similarity	NPC475211
0.766	Intermediate Similarity	NPC10274
0.766	Intermediate Similarity	NPC88337
0.7653	Intermediate Similarity	NPC253995
0.7647	Intermediate Similarity	NPC126753
0.7647	Intermediate Similarity	NPC166993
0.7647	Intermediate Similarity	NPC55508
0.764	Intermediate Similarity	NPC328639
0.764	Intermediate Similarity	NPC190940
0.764	Intermediate Similarity	NPC280781
0.764	Intermediate Similarity	NPC329490
0.764	Intermediate Similarity	NPC73515
0.764	Intermediate Similarity	NPC48756
0.764	Intermediate Similarity	NPC58631
0.7634	Intermediate Similarity	NPC56777
0.7634	Intermediate Similarity	NPC201607
0.7634	Intermediate Similarity	NPC236459
0.7634	Intermediate Similarity	NPC473319
0.7634	Intermediate Similarity	NPC3032
0.7634	Intermediate Similarity	NPC131104
0.7629	Intermediate Similarity	NPC252056
0.7629	Intermediate Similarity	NPC471777
0.7624	Intermediate Similarity	NPC65523
0.7624	Intermediate Similarity	NPC283850
0.7619	Intermediate Similarity	NPC42658
0.7619	Intermediate Similarity	NPC477492
0.7614	Intermediate Similarity	NPC81074
0.7614	Intermediate Similarity	NPC477282
0.7614	Intermediate Similarity	NPC476176
0.7609	Intermediate Similarity	NPC474008

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 NPC476379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	549
0.1-0.2	3498
0.2-0.3	3227
0.3-0.4	1130
0.4-0.5	430
0.5-0.6	233
0.6-0.7	68
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7907	Intermediate Similarity	NPD6114	Approved
0.7907	Intermediate Similarity	NPD6697	Approved
0.7907	Intermediate Similarity	NPD6115	Approved
0.7907	Intermediate Similarity	NPD6118	Approved
0.7843	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6116	Phase 1
0.7745	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6117	Approved
0.7442	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD1700	Approved
0.717	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3703	Phase 2
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD371	Approved
0.6977	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6921	Approved
0.6909	Remote Similarity	NPD8133	Approved
0.6869	Remote Similarity	NPD8034	Phase 2
0.6869	Remote Similarity	NPD8035	Phase 2
0.6818	Remote Similarity	NPD5777	Approved
0.6778	Remote Similarity	NPD3702	Approved
0.6771	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3669	Approved
0.6737	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4244	Approved
0.6705	Remote Similarity	NPD4245	Approved
0.6702	Remote Similarity	NPD1779	Approved
0.6702	Remote Similarity	NPD1780	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6940	Discontinued
0.6635	Remote Similarity	NPD7638	Approved
0.6629	Remote Similarity	NPD6081	Approved
0.6628	Remote Similarity	NPD4224	Phase 2
0.6591	Remote Similarity	NPD3698	Phase 2
0.6571	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7748	Approved
0.6538	Remote Similarity	NPD7902	Approved
0.6535	Remote Similarity	NPD7515	Phase 2
0.6517	Remote Similarity	NPD4789	Approved
0.6509	Remote Similarity	NPD5344	Discontinued
0.6471	Remote Similarity	NPD8171	Discontinued
0.6466	Remote Similarity	NPD7516	Approved
0.646	Remote Similarity	NPD4632	Approved
0.6455	Remote Similarity	NPD6686	Approved
0.6449	Remote Similarity	NPD7632	Discontinued
0.6435	Remote Similarity	NPD7115	Discovery
0.6422	Remote Similarity	NPD6675	Approved
0.6422	Remote Similarity	NPD6402	Approved
0.6422	Remote Similarity	NPD5739	Approved
0.6422	Remote Similarity	NPD7128	Approved
0.6421	Remote Similarity	NPD6928	Phase 2
0.6417	Remote Similarity	NPD7507	Approved
0.6415	Remote Similarity	NPD8418	Phase 2
0.641	Remote Similarity	NPD6319	Approved
0.6393	Remote Similarity	NPD7319	Approved
0.6387	Remote Similarity	NPD8328	Phase 3
0.6383	Remote Similarity	NPD3671	Phase 1
0.6379	Remote Similarity	NPD7328	Approved
0.6379	Remote Similarity	NPD7327	Approved
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6322	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6399	Phase 3
0.6306	Remote Similarity	NPD7320	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6304	Remote Similarity	NPD1811	Approved
0.6304	Remote Similarity	NPD1810	Approved
0.6273	Remote Similarity	NPD6008	Approved
0.6264	Remote Similarity	NPD4758	Discontinued
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6372	Approved
0.6216	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD5701	Approved
0.6211	Remote Similarity	NPD5364	Discontinued
0.6207	Remote Similarity	NPD7909	Approved
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6179	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD6009	Approved
0.6148	Remote Similarity	NPD6616	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6134	Remote Similarity	NPD6059	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6117	Remote Similarity	NPD6698	Approved
0.6117	Remote Similarity	NPD46	Approved
0.6111	Remote Similarity	NPD6648	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6098	Remote Similarity	NPD3728	Approved
0.6098	Remote Similarity	NPD8293	Discontinued
0.6098	Remote Similarity	NPD3730	Approved
0.6098	Remote Similarity	NPD7078	Approved
0.6098	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6882	Approved
0.6083	Remote Similarity	NPD8379	Approved
0.6083	Remote Similarity	NPD8335	Approved
0.6083	Remote Similarity	NPD8380	Approved
0.6083	Remote Similarity	NPD8378	Approved
0.6083	Remote Similarity	NPD8296	Approved
0.6083	Remote Similarity	NPD5983	Phase 2
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6033	Remote Similarity	NPD6370	Approved
0.6019	Remote Similarity	NPD4225	Approved
0.6018	Remote Similarity	NPD6011	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8377	Approved
0.5978	Remote Similarity	NPD2686	Approved
0.5978	Remote Similarity	NPD2687	Approved
0.5978	Remote Similarity	NPD2254	Approved
0.5978	Remote Similarity	NPD4787	Phase 1
0.595	Remote Similarity	NPD8033	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5918	Remote Similarity	NPD7525	Registered
0.5913	Remote Similarity	NPD4634	Approved
0.5905	Remote Similarity	NPD6411	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.59	Remote Similarity	NPD4788	Approved
0.5882	Remote Similarity	NPD3618	Phase 1
0.5865	Remote Similarity	NPD5328	Approved
0.5849	Remote Similarity	NPD4202	Approved
0.5842	Remote Similarity	NPD4786	Approved
0.5825	Remote Similarity	NPD7524	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD4700	Approved
0.5816	Remote Similarity	NPD7645	Phase 2
0.581	Remote Similarity	NPD3168	Discontinued
0.58	Remote Similarity	NPD3667	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.5769	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4159	Approved
0.5761	Remote Similarity	NPD229	Approved
0.5755	Remote Similarity	NPD6079	Approved
0.5747	Remote Similarity	NPD3198	Approved
0.5741	Remote Similarity	NPD5695	Phase 3
0.5741	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD7334	Approved
0.5728	Remote Similarity	NPD6684	Approved
0.5728	Remote Similarity	NPD5330	Approved
0.5728	Remote Similarity	NPD6409	Approved
0.5728	Remote Similarity	NPD7146	Approved
0.5728	Remote Similarity	NPD7521	Approved
0.5727	Remote Similarity	NPD5696	Approved
0.5726	Remote Similarity	NPD6067	Discontinued
0.5714	Remote Similarity	NPD4802	Phase 2
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD8086	Approved
0.5714	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD8084	Approved
0.5714	Remote Similarity	NPD8138	Approved
0.5714	Remote Similarity	NPD6101	Approved
0.5714	Remote Similarity	NPD4238	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8083	Approved
0.5702	Remote Similarity	NPD6335	Approved
0.5702	Remote Similarity	NPD6920	Discontinued
0.5701	Remote Similarity	NPD5778	Approved
0.5701	Remote Similarity	NPD5779	Approved
0.5691	Remote Similarity	NPD6909	Approved
0.5691	Remote Similarity	NPD7503	Approved
0.5691	Remote Similarity	NPD6908	Approved
0.5673	Remote Similarity	NPD3573	Approved
0.5669	Remote Similarity	NPD6033	Approved
0.5664	Remote Similarity	NPD8276	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