NPASS Compound

Structure

NPC476435 OpenBabel07101719242D 25 28 0 0 1 0 0 0 0 0999 V2000 -2.4143 -0.8876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 -1.6211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3080 3.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1074 0.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5086 1.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5086 2.1271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2939 2.1271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4180 -0.8014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1074 2.1271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3080 3.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 2.5316 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1074 1.3181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2939 1.3181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8605 1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 4.2636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3080 3.3976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1599 1.8181 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 12 1 0 0 0 0 2 12 1 0 0 0 0 4 17 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 13 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 13 16 1 1 0 0 0 13 17 1 0 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 3 1 1 0 0 0 17 20 1 6 0 0 0 18 12 1 1 0 0 0 18 25 1 0 0 0 0 19 20 1 6 0 0 0 19 24 1 0 0 0 0 20 11 1 6 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	361.565
LogP:	2.267
LogD:	1.052
LogS:	-3.611
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	6.08
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:	-5.485
MDCK Permeability:	1.7462136383983307e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.284

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	88.91910552978516%
Volume Distribution (VD):	0.485
Pgp-substrate:	11.256953239440918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	2.852
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.331
Carcinogencity:	0.837
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC476435

Natural Product ID:	NPC476435
*Common Name:**	Abiesadine D
IUPAC Name:	n.a.
Synonyms:	Abiesadine D
Standard InCHIKey:	FUMZEAQEADDMAG-CXJUCTJLSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-12(2)18-10-11-20(25-18)17(4)8-5-7-16(3,15(22)23)13(17)6-9-19(20,24)14(18)21/h12-14,21,24H,5-11H2,1-4H3,(H,22,23)/t13-,14-,16+,17-,18-,19-,20+/m0/s1
SMILES:	CC(C)C12CCC3(O1)C4(CCCC(C4CCC3(C2O)O)(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL605193
PubChem CID:	46230020
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[534486]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[534486]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[534486]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[534486]

☑ 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 NPC476435 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	375
0.1-0.2	2865
0.2-0.3	7475
0.3-0.4	14559
0.4-0.5	6285
0.5-0.6	6333
0.6-0.7	3906
0.7-0.8	829
0.8-0.85	52
0.85-0.9	17
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC470114
0.8851	High Similarity	NPC471221
0.8824	High Similarity	NPC477434
0.8804	High Similarity	NPC472144
0.8791	High Similarity	NPC475785
0.8696	High Similarity	NPC472145
0.8681	High Similarity	NPC82633
0.8652	High Similarity	NPC185529
0.8652	High Similarity	NPC472146
0.8636	High Similarity	NPC476379
0.8588	High Similarity	NPC477446
0.8588	High Similarity	NPC470155
0.8588	High Similarity	NPC477447
0.8587	High Similarity	NPC163685
0.8587	High Similarity	NPC235109
0.8587	High Similarity	NPC475765
0.8523	High Similarity	NPC62202
0.8523	High Similarity	NPC213658
0.8523	High Similarity	NPC110365
0.8523	High Similarity	NPC45833
0.8506	High Similarity	NPC476715
0.8506	High Similarity	NPC477445
0.8488	Intermediate Similarity	NPC15091
0.8471	Intermediate Similarity	NPC470156
0.8471	Intermediate Similarity	NPC470154
0.8462	Intermediate Similarity	NPC475307
0.8409	Intermediate Similarity	NPC80700
0.8391	Intermediate Similarity	NPC18953
0.8391	Intermediate Similarity	NPC65133
0.8387	Intermediate Similarity	NPC116683
0.8372	Intermediate Similarity	NPC311642
0.8372	Intermediate Similarity	NPC100366
0.8372	Intermediate Similarity	NPC242771
0.8372	Intermediate Similarity	NPC164289
0.837	Intermediate Similarity	NPC470424
0.8353	Intermediate Similarity	NPC472951
0.8353	Intermediate Similarity	NPC134227
0.8353	Intermediate Similarity	NPC472943
0.8352	Intermediate Similarity	NPC475878
0.8351	Intermediate Similarity	NPC100078
0.8333	Intermediate Similarity	NPC477440
0.8333	Intermediate Similarity	NPC477443
0.8315	Intermediate Similarity	NPC239938
0.8276	Intermediate Similarity	NPC227170
0.8265	Intermediate Similarity	NPC166079
0.8256	Intermediate Similarity	NPC211049
0.8256	Intermediate Similarity	NPC475743
0.8242	Intermediate Similarity	NPC18536
0.8242	Intermediate Similarity	NPC477444
0.8242	Intermediate Similarity	NPC50443
0.8242	Intermediate Similarity	NPC477433
0.8242	Intermediate Similarity	NPC477442
0.8211	Intermediate Similarity	NPC253995
0.8202	Intermediate Similarity	NPC155531
0.8202	Intermediate Similarity	NPC215968
0.8202	Intermediate Similarity	NPC235196
0.8202	Intermediate Similarity	NPC83242
0.8202	Intermediate Similarity	NPC228593
0.8182	Intermediate Similarity	NPC473299
0.8182	Intermediate Similarity	NPC291310
0.8161	Intermediate Similarity	NPC102156
0.8161	Intermediate Similarity	NPC148740
0.8152	Intermediate Similarity	NPC216137
0.8144	Intermediate Similarity	NPC213528
0.8144	Intermediate Similarity	NPC244969
0.8132	Intermediate Similarity	NPC56962
0.8132	Intermediate Similarity	NPC24705
0.8132	Intermediate Similarity	NPC61688
0.8118	Intermediate Similarity	NPC252483
0.8118	Intermediate Similarity	NPC191345
0.8111	Intermediate Similarity	NPC470920
0.8105	Intermediate Similarity	NPC266417
0.8095	Intermediate Similarity	NPC474020
0.809	Intermediate Similarity	NPC473350
0.809	Intermediate Similarity	NPC478111
0.809	Intermediate Similarity	NPC477205
0.8085	Intermediate Similarity	NPC17336
0.8081	Intermediate Similarity	NPC306776
0.8072	Intermediate Similarity	NPC55508
0.8046	Intermediate Similarity	NPC116320
0.8046	Intermediate Similarity	NPC119922
0.8022	Intermediate Similarity	NPC221993
0.8022	Intermediate Similarity	NPC470872
0.8	Intermediate Similarity	NPC474215
0.8	Intermediate Similarity	NPC475729
0.8	Intermediate Similarity	NPC307865
0.8	Intermediate Similarity	NPC477283
0.8	Intermediate Similarity	NPC256227
0.8	Intermediate Similarity	NPC472272
0.8	Intermediate Similarity	NPC476717
0.7978	Intermediate Similarity	NPC219535
0.7978	Intermediate Similarity	NPC237938
0.7959	Intermediate Similarity	NPC471254
0.7955	Intermediate Similarity	NPC202688
0.7955	Intermediate Similarity	NPC60018
0.7955	Intermediate Similarity	NPC154043
0.7955	Intermediate Similarity	NPC121121
0.7935	Intermediate Similarity	NPC471459
0.7935	Intermediate Similarity	NPC67653
0.7931	Intermediate Similarity	NPC125366
0.7917	Intermediate Similarity	NPC471241
0.7917	Intermediate Similarity	NPC472273
0.7912	Intermediate Similarity	NPC263802
0.7912	Intermediate Similarity	NPC5943
0.7907	Intermediate Similarity	NPC43463
0.7889	Intermediate Similarity	NPC266651
0.7889	Intermediate Similarity	NPC131350
0.7882	Intermediate Similarity	NPC136424
0.7872	Intermediate Similarity	NPC182740
0.7872	Intermediate Similarity	NPC256104
0.7872	Intermediate Similarity	NPC211845
0.7872	Intermediate Similarity	NPC122083
0.7865	Intermediate Similarity	NPC111582
0.7865	Intermediate Similarity	NPC477285
0.7857	Intermediate Similarity	NPC470151
0.7843	Intermediate Similarity	NPC154906
0.7841	Intermediate Similarity	NPC476071
0.7841	Intermediate Similarity	NPC58631
0.7841	Intermediate Similarity	NPC190940
0.7835	Intermediate Similarity	NPC211087
0.7826	Intermediate Similarity	NPC226491
0.7826	Intermediate Similarity	NPC477614
0.7816	Intermediate Similarity	NPC201276
0.7816	Intermediate Similarity	NPC80891
0.7812	Intermediate Similarity	NPC476728
0.781	Intermediate Similarity	NPC470116
0.781	Intermediate Similarity	NPC470115
0.7802	Intermediate Similarity	NPC131365
0.7802	Intermediate Similarity	NPC92139
0.7802	Intermediate Similarity	NPC471411
0.7802	Intermediate Similarity	NPC103782
0.7802	Intermediate Similarity	NPC302111
0.7802	Intermediate Similarity	NPC477441
0.7802	Intermediate Similarity	NPC474008
0.7802	Intermediate Similarity	NPC471410
0.7802	Intermediate Similarity	NPC114378
0.78	Intermediate Similarity	NPC471293
0.78	Intermediate Similarity	NPC301787
0.7791	Intermediate Similarity	NPC143250
0.7789	Intermediate Similarity	NPC329713
0.7789	Intermediate Similarity	NPC309127
0.7789	Intermediate Similarity	NPC217567
0.7789	Intermediate Similarity	NPC247877
0.7789	Intermediate Similarity	NPC477495
0.7789	Intermediate Similarity	NPC76136
0.7778	Intermediate Similarity	NPC470172
0.7778	Intermediate Similarity	NPC471044
0.7778	Intermediate Similarity	NPC79308
0.7778	Intermediate Similarity	NPC473336
0.7766	Intermediate Similarity	NPC474065
0.7765	Intermediate Similarity	NPC472950
0.7765	Intermediate Similarity	NPC472952
0.7755	Intermediate Similarity	NPC477656
0.7755	Intermediate Similarity	NPC477655
0.7753	Intermediate Similarity	NPC477286
0.7753	Intermediate Similarity	NPC286719
0.7742	Intermediate Similarity	NPC200580
0.7727	Intermediate Similarity	NPC471217
0.7727	Intermediate Similarity	NPC471216
0.7727	Intermediate Similarity	NPC186594
0.7723	Intermediate Similarity	NPC222833
0.7714	Intermediate Similarity	NPC97002
0.7708	Intermediate Similarity	NPC62407
0.7708	Intermediate Similarity	NPC287354
0.7701	Intermediate Similarity	NPC34046
0.7701	Intermediate Similarity	NPC324700
0.7701	Intermediate Similarity	NPC171426
0.7701	Intermediate Similarity	NPC80089
0.7701	Intermediate Similarity	NPC224802
0.77	Intermediate Similarity	NPC473406
0.77	Intermediate Similarity	NPC61442
0.77	Intermediate Similarity	NPC471253
0.7692	Intermediate Similarity	NPC157476
0.7692	Intermediate Similarity	NPC235402
0.7684	Intermediate Similarity	NPC472147
0.7684	Intermediate Similarity	NPC476189
0.7684	Intermediate Similarity	NPC472148
0.7684	Intermediate Similarity	NPC474379
0.7677	Intermediate Similarity	NPC259654
0.7677	Intermediate Similarity	NPC298266
0.7667	Intermediate Similarity	NPC269684
0.7667	Intermediate Similarity	NPC476721
0.7667	Intermediate Similarity	NPC292458
0.7667	Intermediate Similarity	NPC268578
0.7667	Intermediate Similarity	NPC217559
0.766	Intermediate Similarity	NPC475211
0.766	Intermediate Similarity	NPC88337
0.766	Intermediate Similarity	NPC77756
0.7647	Intermediate Similarity	NPC126753
0.7647	Intermediate Similarity	NPC59530
0.7647	Intermediate Similarity	NPC166993
0.7642	Intermediate Similarity	NPC117712
0.7642	Intermediate Similarity	NPC79193
0.764	Intermediate Similarity	NPC328639
0.764	Intermediate Similarity	NPC280781
0.764	Intermediate Similarity	NPC329490
0.764	Intermediate Similarity	NPC48756
0.764	Intermediate Similarity	NPC71541
0.764	Intermediate Similarity	NPC12933
0.7634	Intermediate Similarity	NPC48824

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 NPC476435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	3304
0.2-0.3	3505
0.3-0.4	1144
0.4-0.5	395
0.5-0.6	250
0.6-0.7	124
0.7-0.8	13
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
0.7701	Intermediate Similarity	NPD6697	Approved
0.7701	Intermediate Similarity	NPD6115	Approved
0.7701	Intermediate Similarity	NPD6118	Approved
0.7701	Intermediate Similarity	NPD6114	Approved
0.7677	Intermediate Similarity	NPD1700	Approved
0.7573	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6117	Approved
0.7386	Intermediate Similarity	NPD6116	Phase 1
0.7356	Intermediate Similarity	NPD3703	Phase 2
0.7282	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3702	Approved
0.6852	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD371	Approved
0.6783	Remote Similarity	NPD6921	Approved
0.6782	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5777	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6607	Remote Similarity	NPD4632	Approved
0.6607	Remote Similarity	NPD8133	Approved
0.6606	Remote Similarity	NPD7320	Approved
0.6598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6574	Remote Similarity	NPD5739	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6319	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6535	Remote Similarity	NPD8035	Phase 2
0.6535	Remote Similarity	NPD8034	Phase 2
0.6529	Remote Similarity	NPD7319	Approved
0.6526	Remote Similarity	NPD1780	Approved
0.6526	Remote Similarity	NPD1779	Approved
0.6518	Remote Similarity	NPD8297	Approved
0.6517	Remote Similarity	NPD4245	Approved
0.6517	Remote Similarity	NPD4244	Approved
0.6514	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD7078	Approved
0.6477	Remote Similarity	NPD5360	Phase 3
0.6477	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD8171	Discontinued
0.6455	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD6899	Approved
0.6446	Remote Similarity	NPD7736	Approved
0.6444	Remote Similarity	NPD6081	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6437	Remote Similarity	NPD4224	Phase 2
0.6422	Remote Similarity	NPD6008	Approved
0.6421	Remote Similarity	NPD6928	Phase 2
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.6404	Remote Similarity	NPD3698	Phase 2
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6395	Remote Similarity	NPD7909	Approved
0.6392	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3669	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6356	Remote Similarity	NPD6015	Approved
0.6356	Remote Similarity	NPD6016	Approved
0.6348	Remote Similarity	NPD6940	Discontinued
0.6339	Remote Similarity	NPD6883	Approved
0.6339	Remote Similarity	NPD7290	Approved
0.6339	Remote Similarity	NPD7102	Approved
0.6333	Remote Similarity	NPD4789	Approved
0.633	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4225	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6303	Remote Similarity	NPD5988	Approved
0.6296	Remote Similarity	NPD7632	Discontinued
0.6293	Remote Similarity	NPD6009	Approved
0.6292	Remote Similarity	NPD229	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6847	Approved
0.6283	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6283	Remote Similarity	NPD6617	Approved
0.6283	Remote Similarity	NPD8130	Phase 1
0.6262	Remote Similarity	NPD8418	Phase 2
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6882	Approved
0.6218	Remote Similarity	NPD5983	Phase 2
0.6216	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD7515	Phase 2
0.6211	Remote Similarity	NPD3671	Phase 1
0.6186	Remote Similarity	NPD7516	Approved
0.6176	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7115	Discovery
0.6148	Remote Similarity	NPD6336	Discontinued
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7327	Approved
0.6102	Remote Similarity	NPD7328	Approved
0.6098	Remote Similarity	NPD3728	Approved
0.6098	Remote Similarity	NPD3730	Approved
0.6098	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4758	Discontinued
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD4755	Approved
0.6075	Remote Similarity	NPD6083	Phase 2
0.6075	Remote Similarity	NPD7902	Approved
0.6058	Remote Similarity	NPD6079	Approved
0.6058	Remote Similarity	NPD6411	Approved
0.6053	Remote Similarity	NPD4634	Approved
0.6048	Remote Similarity	NPD6033	Approved
0.6042	Remote Similarity	NPD5364	Discontinued
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.598	Remote Similarity	NPD7524	Approved
0.5963	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.5957	Remote Similarity	NPD1810	Approved
0.5957	Remote Similarity	NPD1811	Approved
0.5955	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8335	Approved
0.595	Remote Similarity	NPD8380	Approved
0.595	Remote Similarity	NPD8378	Approved
0.595	Remote Similarity	NPD8296	Approved
0.595	Remote Similarity	NPD8379	Approved
0.5932	Remote Similarity	NPD6274	Approved
0.593	Remote Similarity	NPD3198	Approved
0.5917	Remote Similarity	NPD7100	Approved
0.5917	Remote Similarity	NPD7101	Approved
0.5909	Remote Similarity	NPD5344	Discontinued
0.5888	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3618	Phase 1
0.5876	Remote Similarity	NPD4802	Phase 2
0.5876	Remote Similarity	NPD4238	Approved
0.5868	Remote Similarity	NPD8377	Approved
0.5868	Remote Similarity	NPD8294	Approved
0.5865	Remote Similarity	NPD6101	Approved
0.5865	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD8085	Approved
0.5856	Remote Similarity	NPD8082	Approved
0.5856	Remote Similarity	NPD8084	Approved
0.5856	Remote Similarity	NPD8083	Approved
0.5856	Remote Similarity	NPD5211	Phase 2
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.5856	Remote Similarity	NPD8139	Approved
0.5856	Remote Similarity	NPD8086	Approved
0.5856	Remote Similarity	NPD8138	Approved
0.5854	Remote Similarity	NPD6067	Discontinued
0.5842	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD6335	Approved
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD5221	Approved
0.5825	Remote Similarity	NPD3573	Approved
0.582	Remote Similarity	NPD8513	Phase 3
0.582	Remote Similarity	NPD8516	Approved
0.582	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6909	Approved
0.582	Remote Similarity	NPD8515	Approved
0.582	Remote Similarity	NPD8517	Approved
0.582	Remote Similarity	NPD6908	Approved
0.582	Remote Similarity	NPD8033	Approved
0.5812	Remote Similarity	NPD6053	Discontinued
0.5806	Remote Similarity	NPD4787	Phase 1
0.5804	Remote Similarity	NPD5174	Approved
0.5804	Remote Similarity	NPD8275	Approved
0.5804	Remote Similarity	NPD8276	Approved
0.5804	Remote Similarity	NPD5175	Approved
0.58	Remote Similarity	NPD3667	Approved
0.5798	Remote Similarity	NPD6868	Approved
0.5794	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7900	Approved
0.578	Remote Similarity	NPD5173	Approved
0.5769	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6903	Approved
0.5766	Remote Similarity	NPD5223	Approved
0.5755	Remote Similarity	NPD7983	Approved
0.5755	Remote Similarity	NPD7637	Suspended

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