NPASS Compound

Structure

NPC217983 OpenBabel07101718322D 24 26 0 0 1 0 0 0 0 0999 V2000 3.2475 3.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5430 5.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8370 3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6923 2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4385 4.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2371 2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 0.9705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9002 1.0288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5068 2.5457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2910 1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4769 1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3232 0.9463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5249 3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9999 0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7159 4.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 -0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 2.9524 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 8 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 10 2 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 5 1 6 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 7 1 1 0 0 0 12 15 1 0 0 0 0 13 20 1 6 0 0 0 14 16 1 0 0 0 0 14 23 1 6 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	342.28
LogP:	1.441
LogD:	1.585
LogS:	-2.827
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	4.897
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.923
MDCK Permeability:	0.00011709238606272265
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	64.56531524658203%
Volume Distribution (VD):	1.061
Pgp-substrate:	36.404396057128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	7.761
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.635
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.11
Carcinogencity:	0.055
Eye Corrosion:	0.037
Eye Irritation:	0.095
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC217983

Natural Product ID:	NPC217983
*Common Name:**	3Alpha,8Alphadihydroxy-1Alphah,5Alphah,6Betah,7Alphah,11Betah-Guai-4(15),10(14)-Dien-6,12-Olide 8-O-(2-Methyl)Acrylate
IUPAC Name:	[(3S,3aR,4S,6aR,8R,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:
Standard InCHIKey:	IXOAQFFFKPCXLB-OPCFMFSHSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-8(2)18(21)23-14-6-9(3)12-7-13(20)10(4)15(12)17-16(14)11(5)19(22)24-17/h11-17,20H,1,3-4,6-7H2,2,5H3/t11-,12-,13+,14-,15-,16+,17+/m0/s1
SMILES:	O=C1O[C@H]2[C@H]([C@@H]1C)[C@H](CC(=C)[C@H]1[C@@H]2C(=C)[C@@H](C1)O)OC(=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463131
PubChem CID:	11313565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921425]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9587	Saussurea laniceps	Species	Asteraceae	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	8

Activity Type	# Activity
NON-MOLECULAR	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	33.78	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	36.13	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	30.59	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.04	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	34.78	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	31.12	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	20.58	cpm	PMID[549988]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.08	cpm	PMID[549988]

☑ 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 NPC217983 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	234
0.1-0.2	1631
0.2-0.3	5993
0.3-0.4	14824
0.4-0.5	9838
0.5-0.6	6903
0.6-0.7	2602
0.7-0.8	500
0.8-0.85	82
0.85-0.9	50
0.9-0.95	30
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC207114
0.9762	High Similarity	NPC19087
0.9756	High Similarity	NPC187661
0.9647	High Similarity	NPC184063
0.9643	High Similarity	NPC38392
0.9529	High Similarity	NPC54065
0.9529	High Similarity	NPC297474
0.9512	High Similarity	NPC194859
0.9512	High Similarity	NPC224386
0.9419	High Similarity	NPC35959
0.9419	High Similarity	NPC293001
0.9419	High Similarity	NPC133888
0.9419	High Similarity	NPC57304
0.9419	High Similarity	NPC63193
0.9419	High Similarity	NPC475925
0.9419	High Similarity	NPC29821
0.9419	High Similarity	NPC171360
0.9412	High Similarity	NPC155935
0.9412	High Similarity	NPC215556
0.939	High Similarity	NPC128246
0.9302	High Similarity	NPC216284
0.9302	High Similarity	NPC35809
0.9294	High Similarity	NPC79549
0.9268	High Similarity	NPC246076
0.9146	High Similarity	NPC126248
0.9111	High Similarity	NPC474313
0.9101	High Similarity	NPC476053
0.9101	High Similarity	NPC472873
0.9091	High Similarity	NPC258216
0.9059	High Similarity	NPC56593
0.9059	High Similarity	NPC304558
0.9	High Similarity	NPC91771
0.9	High Similarity	NPC142529
0.9	High Similarity	NPC24956
0.9	High Similarity	NPC18019
0.8989	High Similarity	NPC198853
0.8977	High Similarity	NPC155215
0.8953	High Similarity	NPC24728
0.8953	High Similarity	NPC118601
0.8941	High Similarity	NPC300082
0.8941	High Similarity	NPC204105
0.8941	High Similarity	NPC284534
0.8929	High Similarity	NPC111409
0.8901	High Similarity	NPC471150
0.8889	High Similarity	NPC163228
0.8889	High Similarity	NPC170120
0.8889	High Similarity	NPC213698
0.8851	High Similarity	NPC178875
0.8851	High Similarity	NPC471149
0.8837	High Similarity	NPC309757
0.8837	High Similarity	NPC64153
0.8837	High Similarity	NPC236692
0.8778	High Similarity	NPC470013
0.8778	High Similarity	NPC262133
0.8778	High Similarity	NPC473331
0.8778	High Similarity	NPC470010
0.8778	High Similarity	NPC127019
0.8778	High Similarity	NPC323008
0.8764	High Similarity	NPC133698
0.8764	High Similarity	NPC131209
0.875	High Similarity	NPC283409
0.875	High Similarity	NPC472872
0.8706	High Similarity	NPC245665
0.8696	High Similarity	NPC311904
0.8696	High Similarity	NPC161493
0.8681	High Similarity	NPC52044
0.8681	High Similarity	NPC304886
0.8681	High Similarity	NPC67584
0.8667	High Similarity	NPC60386
0.8667	High Similarity	NPC308656
0.8667	High Similarity	NPC475788
0.8667	High Similarity	NPC473234
0.8667	High Similarity	NPC473263
0.8667	High Similarity	NPC200237
0.8667	High Similarity	NPC473273
0.8621	High Similarity	NPC470242
0.8617	High Similarity	NPC171759
0.8617	High Similarity	NPC150923
0.8602	High Similarity	NPC49833
0.8602	High Similarity	NPC249171
0.8587	High Similarity	NPC213078
0.8571	High Similarity	NPC477131
0.8556	High Similarity	NPC286341
0.8556	High Similarity	NPC191339
0.8539	High Similarity	NPC12872
0.8539	High Similarity	NPC168679
0.8526	High Similarity	NPC80144
0.8511	High Similarity	NPC186861
0.8511	High Similarity	NPC471381
0.8495	Intermediate Similarity	NPC181151
0.8495	Intermediate Similarity	NPC304445
0.8495	Intermediate Similarity	NPC236580
0.8462	Intermediate Similarity	NPC153590
0.8438	Intermediate Similarity	NPC473148
0.8427	Intermediate Similarity	NPC91248
0.8421	Intermediate Similarity	NPC67296
0.8409	Intermediate Similarity	NPC67493
0.8409	Intermediate Similarity	NPC162071
0.8404	Intermediate Similarity	NPC221615
0.8404	Intermediate Similarity	NPC45125
0.8387	Intermediate Similarity	NPC474297
0.8353	Intermediate Similarity	NPC156658
0.8353	Intermediate Similarity	NPC258965
0.8353	Intermediate Similarity	NPC51507
0.8333	Intermediate Similarity	NPC86077
0.8315	Intermediate Similarity	NPC270270
0.8315	Intermediate Similarity	NPC201658
0.8315	Intermediate Similarity	NPC186148
0.8315	Intermediate Similarity	NPC190753
0.8298	Intermediate Similarity	NPC213947
0.8298	Intermediate Similarity	NPC170143
0.8298	Intermediate Similarity	NPC108475
0.8295	Intermediate Similarity	NPC235792
0.8293	Intermediate Similarity	NPC143979
0.8293	Intermediate Similarity	NPC320537
0.828	Intermediate Similarity	NPC167893
0.8276	Intermediate Similarity	NPC54468
0.8265	Intermediate Similarity	NPC54737
0.8265	Intermediate Similarity	NPC44004
0.8261	Intermediate Similarity	NPC135776
0.8261	Intermediate Similarity	NPC472874
0.8242	Intermediate Similarity	NPC206614
0.8242	Intermediate Similarity	NPC37607
0.8242	Intermediate Similarity	NPC301969
0.8242	Intermediate Similarity	NPC474323
0.8222	Intermediate Similarity	NPC58219
0.8222	Intermediate Similarity	NPC224652
0.8222	Intermediate Similarity	NPC177629
0.8202	Intermediate Similarity	NPC238593
0.8191	Intermediate Similarity	NPC476009
0.8191	Intermediate Similarity	NPC126156
0.8182	Intermediate Similarity	NPC156485
0.8132	Intermediate Similarity	NPC295312
0.8132	Intermediate Similarity	NPC4986
0.8132	Intermediate Similarity	NPC92974
0.8125	Intermediate Similarity	NPC70865
0.81	Intermediate Similarity	NPC68248
0.809	Intermediate Similarity	NPC165162
0.809	Intermediate Similarity	NPC255307
0.8085	Intermediate Similarity	NPC475900
0.8081	Intermediate Similarity	NPC243998
0.8081	Intermediate Similarity	NPC166115
0.8065	Intermediate Similarity	NPC475838
0.8065	Intermediate Similarity	NPC475912
0.8065	Intermediate Similarity	NPC228451
0.8065	Intermediate Similarity	NPC125674
0.8046	Intermediate Similarity	NPC47635
0.8043	Intermediate Similarity	NPC129419
0.8043	Intermediate Similarity	NPC475855
0.8023	Intermediate Similarity	NPC19841
0.8022	Intermediate Similarity	NPC202672
0.802	Intermediate Similarity	NPC59489
0.802	Intermediate Similarity	NPC139838
0.8	Intermediate Similarity	NPC208223
0.8	Intermediate Similarity	NPC475019
0.8	Intermediate Similarity	NPC305475
0.8	Intermediate Similarity	NPC475461
0.8	Intermediate Similarity	NPC284518
0.8	Intermediate Similarity	NPC474949
0.7979	Intermediate Similarity	NPC474338
0.7979	Intermediate Similarity	NPC474247
0.7978	Intermediate Similarity	NPC114979
0.7978	Intermediate Similarity	NPC474780
0.7978	Intermediate Similarity	NPC476804
0.7978	Intermediate Similarity	NPC191476
0.7957	Intermediate Similarity	NPC184463
0.7957	Intermediate Similarity	NPC12172
0.7957	Intermediate Similarity	NPC208886
0.7955	Intermediate Similarity	NPC89555
0.7935	Intermediate Similarity	NPC268298
0.7935	Intermediate Similarity	NPC32922
0.7931	Intermediate Similarity	NPC73052
0.7931	Intermediate Similarity	NPC6823
0.7931	Intermediate Similarity	NPC290508
0.7931	Intermediate Similarity	NPC293418
0.7917	Intermediate Similarity	NPC261372
0.7917	Intermediate Similarity	NPC58267
0.7917	Intermediate Similarity	NPC263674
0.7917	Intermediate Similarity	NPC169205
0.7912	Intermediate Similarity	NPC160138
0.79	Intermediate Similarity	NPC223450
0.7895	Intermediate Similarity	NPC224689
0.7895	Intermediate Similarity	NPC14961
0.7895	Intermediate Similarity	NPC36954
0.7895	Intermediate Similarity	NPC259042
0.7895	Intermediate Similarity	NPC157686
0.7895	Intermediate Similarity	NPC270013
0.7889	Intermediate Similarity	NPC329749
0.7885	Intermediate Similarity	NPC273242
0.7879	Intermediate Similarity	NPC221421
0.7879	Intermediate Similarity	NPC124881
0.7872	Intermediate Similarity	NPC179746
0.7872	Intermediate Similarity	NPC212486
0.7872	Intermediate Similarity	NPC81419
0.7865	Intermediate Similarity	NPC128429
0.7865	Intermediate Similarity	NPC473390
0.7865	Intermediate Similarity	NPC250315
0.7865	Intermediate Similarity	NPC131669
0.7849	Intermediate Similarity	NPC144133
0.7849	Intermediate Similarity	NPC469368

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 NPC217983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	2397
0.2-0.3	3870
0.3-0.4	1815
0.4-0.5	489
0.5-0.6	253
0.6-0.7	35
0.7-0.8	11
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
0.8132	Intermediate Similarity	NPD1695	Approved
0.7822	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4249	Approved
0.7527	Intermediate Similarity	NPD4250	Approved
0.7527	Intermediate Similarity	NPD4251	Approved
0.7429	Intermediate Similarity	NPD6371	Approved
0.7292	Intermediate Similarity	NPD5785	Approved
0.7283	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7128	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5363	Approved
0.7113	Intermediate Similarity	NPD46	Approved
0.7113	Intermediate Similarity	NPD6698	Approved
0.7097	Intermediate Similarity	NPD7154	Phase 3
0.6989	Remote Similarity	NPD4270	Approved
0.6989	Remote Similarity	NPD4269	Approved
0.6989	Remote Similarity	NPD6435	Approved
0.6957	Remote Similarity	NPD4821	Approved
0.6957	Remote Similarity	NPD4820	Approved
0.6957	Remote Similarity	NPD4822	Approved
0.6957	Remote Similarity	NPD4819	Approved
0.6947	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4271	Approved
0.6923	Remote Similarity	NPD4268	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6882	Remote Similarity	NPD5369	Approved
0.6875	Remote Similarity	NPD5786	Approved
0.6796	Remote Similarity	NPD7638	Approved
0.6774	Remote Similarity	NPD4252	Approved
0.6774	Remote Similarity	NPD5368	Approved
0.6768	Remote Similarity	NPD7838	Discovery
0.6737	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD5331	Approved
0.6733	Remote Similarity	NPD5282	Discontinued
0.6702	Remote Similarity	NPD4790	Discontinued
0.67	Remote Similarity	NPD7983	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6606	Remote Similarity	NPD6686	Approved
0.6577	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6399	Phase 3
0.6449	Remote Similarity	NPD7632	Discontinued
0.6422	Remote Similarity	NPD6008	Approved
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD8035	Phase 2
0.6373	Remote Similarity	NPD7637	Suspended
0.6355	Remote Similarity	NPD5344	Discontinued
0.6316	Remote Similarity	NPD8133	Approved
0.631	Remote Similarity	NPD3198	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD1694	Approved
0.6226	Remote Similarity	NPD6083	Phase 2
0.6226	Remote Similarity	NPD6084	Phase 2
0.6216	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD5697	Approved
0.6211	Remote Similarity	NPD4802	Phase 2
0.6211	Remote Similarity	NPD4238	Approved
0.619	Remote Similarity	NPD5695	Phase 3
0.6176	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5696	Approved
0.6162	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6148	Remote Similarity	NPD7507	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6132	Remote Similarity	NPD7839	Suspended
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD6648	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6372	Approved
0.6106	Remote Similarity	NPD6373	Approved
0.61	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD8513	Phase 3
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8517	Approved
0.6078	Remote Similarity	NPD6903	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6066	Remote Similarity	NPD7492	Approved
0.6061	Remote Similarity	NPD6695	Phase 3
0.6061	Remote Similarity	NPD4788	Approved
0.6058	Remote Similarity	NPD6411	Approved
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD7146	Approved
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD6684	Approved
0.6034	Remote Similarity	NPD4632	Approved
0.6018	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6011	Approved
0.6016	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5968	Remote Similarity	NPD7078	Approved
0.596	Remote Similarity	NPD3667	Approved
0.5952	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8267	Approved
0.595	Remote Similarity	NPD8266	Approved
0.595	Remote Similarity	NPD8269	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.595	Remote Similarity	NPD8268	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5929	Remote Similarity	NPD6685	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7736	Approved
0.5905	Remote Similarity	NPD5281	Approved
0.5905	Remote Similarity	NPD5693	Phase 1
0.5905	Remote Similarity	NPD5284	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.5902	Remote Similarity	NPD6370	Approved
0.5893	Remote Similarity	NPD5141	Approved
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5888	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD6009	Approved
0.5868	Remote Similarity	NPD6059	Approved
0.5865	Remote Similarity	NPD4753	Phase 2
0.5865	Remote Similarity	NPD5370	Suspended
0.5859	Remote Similarity	NPD6845	Suspended
0.5842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4786	Approved
0.584	Remote Similarity	NPD8293	Discontinued
0.584	Remote Similarity	NPD8074	Phase 3
0.5833	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD7328	Approved
0.5825	Remote Similarity	NPD7524	Approved
0.5825	Remote Similarity	NPD7750	Discontinued
0.582	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5983	Phase 2
0.582	Remote Similarity	NPD8033	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.5816	Remote Similarity	NPD6929	Approved
0.581	Remote Similarity	NPD5207	Approved
0.58	Remote Similarity	NPD5209	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7516	Approved
0.5781	Remote Similarity	NPD7260	Phase 2
0.578	Remote Similarity	NPD4755	Approved
0.578	Remote Similarity	NPD7902	Approved
0.5776	Remote Similarity	NPD6420	Discontinued
0.5769	Remote Similarity	NPD6672	Approved
0.5769	Remote Similarity	NPD5737	Approved
0.576	Remote Similarity	NPD8273	Phase 1
0.5758	Remote Similarity	NPD6931	Approved
0.5758	Remote Similarity	NPD6930	Phase 2
0.5755	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8294	Approved
0.5738	Remote Similarity	NPD8377	Approved
0.5728	Remote Similarity	NPD5279	Phase 3
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD6697	Approved
0.5714	Remote Similarity	NPD6114	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD6115	Approved
0.5714	Remote Similarity	NPD6118	Approved
0.5701	Remote Similarity	NPD4202	Approved
0.5691	Remote Similarity	NPD8296	Approved
0.5691	Remote Similarity	NPD8380	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