NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	0.834
LogD:	1.905
LogS:	-2.145
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.751
Fsp3:	0.8
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:	-4.932
MDCK Permeability:	2.5976083634304814e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.353

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	69.43933868408203%
Volume Distribution (VD):	0.846
Pgp-substrate:	35.758907318115234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.314
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	8.158
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.177
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.635
Skin Sensitization:	0.667
Carcinogencity:	0.682
Eye Corrosion:	0.409
Eye Irritation:	0.647
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC35809

Natural Product ID:	NPC35809
*Common Name:**	Deacetyl-6-Deoxychamissonolide
IUPAC Name:	(3aR,5R,5aS,6S,8R,8aS,9aR)-6,8-dihydroxy-5,8a-dimethyl-1-methylidene-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	BPUNWVGCTMEMKQ-XNPDFKGTSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9-,10+,11-,12-,13-,15-/m1/s1
SMILES:	C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2C[C@]2([C@H]1[C@@H](O)C[C@H]2O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519381
PubChem CID:	12309649
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[16644542]
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO5484	Arnica angustifolia	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
IC50	4

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15200.0	nM	PMID[556274]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[556275]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[556275]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[556275]

☑ 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 NPC35809 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	246
0.1-0.2	1791
0.2-0.3	6486
0.3-0.4	15329
0.4-0.5	8772
0.5-0.6	6929
0.6-0.7	2668
0.7-0.8	338
0.8-0.85	54
0.85-0.9	44
0.9-0.95	23
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC35959
0.9882	High Similarity	NPC63193
0.9882	High Similarity	NPC29821
0.9882	High Similarity	NPC57304
0.9882	High Similarity	NPC293001
0.9882	High Similarity	NPC171360
0.9882	High Similarity	NPC133888
0.9881	High Similarity	NPC155935
0.9765	High Similarity	NPC54065
0.9765	High Similarity	NPC297474
0.9535	High Similarity	NPC216284
0.9524	High Similarity	NPC56593
0.9438	High Similarity	NPC24956
0.9438	High Similarity	NPC18019
0.9419	High Similarity	NPC215556
0.9412	High Similarity	NPC24728
0.9302	High Similarity	NPC207114
0.9302	High Similarity	NPC471149
0.9302	High Similarity	NPC217983
0.9302	High Similarity	NPC79549
0.9294	High Similarity	NPC187661
0.9222	High Similarity	NPC142529
0.9222	High Similarity	NPC91771
0.9205	High Similarity	NPC155215
0.9195	High Similarity	NPC283409
0.9121	High Similarity	NPC311904
0.9111	High Similarity	NPC472873
0.9101	High Similarity	NPC200237
0.9101	High Similarity	NPC258216
0.9091	High Similarity	NPC19087
0.9059	High Similarity	NPC224386
0.9059	High Similarity	NPC194859
0.9	High Similarity	NPC473331
0.8989	High Similarity	NPC184063
0.8977	High Similarity	NPC38392
0.8953	High Similarity	NPC284534
0.8953	High Similarity	NPC300082
0.8953	High Similarity	NPC204105
0.8941	High Similarity	NPC111409
0.8941	High Similarity	NPC128246
0.8913	High Similarity	NPC471150
0.8901	High Similarity	NPC170120
0.8901	High Similarity	NPC213698
0.8901	High Similarity	NPC476053
0.8889	High Similarity	NPC153590
0.8889	High Similarity	NPC60386
0.8889	High Similarity	NPC473263
0.8889	High Similarity	NPC473234
0.8889	High Similarity	NPC473273
0.8889	High Similarity	NPC308656
0.883	High Similarity	NPC171759
0.8824	High Similarity	NPC246076
0.8791	High Similarity	NPC127019
0.8778	High Similarity	NPC286341
0.8778	High Similarity	NPC191339
0.8778	High Similarity	NPC475925
0.8764	High Similarity	NPC12872
0.8764	High Similarity	NPC168679
0.8764	High Similarity	NPC472872
0.875	High Similarity	NPC118601
0.875	High Similarity	NPC201658
0.8723	High Similarity	NPC471381
0.8721	High Similarity	NPC245665
0.871	High Similarity	NPC161493
0.8706	High Similarity	NPC126248
0.8696	High Similarity	NPC52044
0.8696	High Similarity	NPC163228
0.8652	High Similarity	NPC178875
0.8636	High Similarity	NPC236692
0.8636	High Similarity	NPC304558
0.8636	High Similarity	NPC309757
0.8617	High Similarity	NPC45125
0.8602	High Similarity	NPC213078
0.8571	High Similarity	NPC131209
0.8526	High Similarity	NPC186861
0.8511	High Similarity	NPC170143
0.8511	High Similarity	NPC108475
0.8511	High Similarity	NPC474313
0.8511	High Similarity	NPC213947
0.8511	High Similarity	NPC181151
0.8495	Intermediate Similarity	NPC67584
0.8427	Intermediate Similarity	NPC64153
0.8427	Intermediate Similarity	NPC67493
0.8427	Intermediate Similarity	NPC470242
0.8421	Intermediate Similarity	NPC221615
0.8404	Intermediate Similarity	NPC126156
0.8387	Intermediate Similarity	NPC470010
0.8387	Intermediate Similarity	NPC262133
0.8387	Intermediate Similarity	NPC323008
0.8387	Intermediate Similarity	NPC470013
0.8387	Intermediate Similarity	NPC198853
0.8372	Intermediate Similarity	NPC156658
0.8372	Intermediate Similarity	NPC258965
0.837	Intermediate Similarity	NPC133698
0.8333	Intermediate Similarity	NPC270270
0.8295	Intermediate Similarity	NPC54468
0.8283	Intermediate Similarity	NPC54737
0.828	Intermediate Similarity	NPC472874
0.8276	Intermediate Similarity	NPC47635
0.8261	Intermediate Similarity	NPC37607
0.8261	Intermediate Similarity	NPC301969
0.8247	Intermediate Similarity	NPC150923
0.8242	Intermediate Similarity	NPC224652
0.8242	Intermediate Similarity	NPC91248
0.8229	Intermediate Similarity	NPC249171
0.8229	Intermediate Similarity	NPC49833
0.8222	Intermediate Similarity	NPC238593
0.8202	Intermediate Similarity	NPC156485
0.8191	Intermediate Similarity	NPC477131
0.8161	Intermediate Similarity	NPC73052
0.8161	Intermediate Similarity	NPC51507
0.8161	Intermediate Similarity	NPC290508
0.8161	Intermediate Similarity	NPC293418
0.8161	Intermediate Similarity	NPC6823
0.8144	Intermediate Similarity	NPC70865
0.8132	Intermediate Similarity	NPC190753
0.8125	Intermediate Similarity	NPC304445
0.8125	Intermediate Similarity	NPC236580
0.8111	Intermediate Similarity	NPC235792
0.8105	Intermediate Similarity	NPC37408
0.8105	Intermediate Similarity	NPC304886
0.81	Intermediate Similarity	NPC44004
0.8095	Intermediate Similarity	NPC143979
0.8095	Intermediate Similarity	NPC320537
0.8085	Intermediate Similarity	NPC135776
0.8085	Intermediate Similarity	NPC475788
0.8081	Intermediate Similarity	NPC473148
0.8081	Intermediate Similarity	NPC221421
0.8039	Intermediate Similarity	NPC59489
0.8039	Intermediate Similarity	NPC139838
0.8022	Intermediate Similarity	NPC162071
0.8	Intermediate Similarity	NPC225474
0.8	Intermediate Similarity	NPC469596
0.8	Intermediate Similarity	NPC148000
0.8	Intermediate Similarity	NPC471382
0.798	Intermediate Similarity	NPC80144
0.7957	Intermediate Similarity	NPC4986
0.7941	Intermediate Similarity	NPC68248
0.7938	Intermediate Similarity	NPC477949
0.7935	Intermediate Similarity	NPC186148
0.7917	Intermediate Similarity	NPC469873
0.7917	Intermediate Similarity	NPC48803
0.7917	Intermediate Similarity	NPC275960
0.7917	Intermediate Similarity	NPC193645
0.7917	Intermediate Similarity	NPC90121
0.7917	Intermediate Similarity	NPC157686
0.7917	Intermediate Similarity	NPC167893
0.7917	Intermediate Similarity	NPC259042
0.79	Intermediate Similarity	NPC124881
0.7879	Intermediate Similarity	NPC67296
0.7879	Intermediate Similarity	NPC477950
0.7872	Intermediate Similarity	NPC474323
0.7872	Intermediate Similarity	NPC206614
0.7864	Intermediate Similarity	NPC115352
0.7849	Intermediate Similarity	NPC58219
0.7849	Intermediate Similarity	NPC177629
0.7835	Intermediate Similarity	NPC474297
0.7835	Intermediate Similarity	NPC476009
0.7835	Intermediate Similarity	NPC284518
0.7835	Intermediate Similarity	NPC93245
0.783	Intermediate Similarity	NPC471380
0.7822	Intermediate Similarity	NPC203659
0.7816	Intermediate Similarity	NPC208223
0.7812	Intermediate Similarity	NPC24861
0.78	Intermediate Similarity	NPC86077
0.78	Intermediate Similarity	NPC225353
0.7778	Intermediate Similarity	NPC161060
0.7778	Intermediate Similarity	NPC212340
0.7778	Intermediate Similarity	NPC89555
0.7766	Intermediate Similarity	NPC92974
0.7766	Intermediate Similarity	NPC212664
0.7766	Intermediate Similarity	NPC116620
0.7766	Intermediate Similarity	NPC32922
0.7755	Intermediate Similarity	NPC473963
0.7755	Intermediate Similarity	NPC58267
0.7755	Intermediate Similarity	NPC263674
0.7755	Intermediate Similarity	NPC261372
0.7755	Intermediate Similarity	NPC169205
0.7745	Intermediate Similarity	NPC243998
0.7736	Intermediate Similarity	NPC273242
0.7732	Intermediate Similarity	NPC224689
0.7732	Intermediate Similarity	NPC475900
0.7723	Intermediate Similarity	NPC110989
0.7723	Intermediate Similarity	NPC474775
0.7717	Intermediate Similarity	NPC165162
0.7685	Intermediate Similarity	NPC36754
0.7684	Intermediate Similarity	NPC129419
0.7684	Intermediate Similarity	NPC246173
0.7684	Intermediate Similarity	NPC469368
0.7677	Intermediate Similarity	NPC141191
0.7677	Intermediate Similarity	NPC216478
0.767	Intermediate Similarity	NPC26617
0.7664	Intermediate Similarity	NPC121816
0.7664	Intermediate Similarity	NPC123117
0.766	Intermediate Similarity	NPC202672
0.7653	Intermediate Similarity	NPC473964
0.7653	Intermediate Similarity	NPC185553
0.7653	Intermediate Similarity	NPC228766
0.7653	Intermediate Similarity	NPC165528
0.764	Intermediate Similarity	NPC470244

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 NPC35809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	2519
0.2-0.3	3917
0.3-0.4	1672
0.4-0.5	423
0.5-0.6	276
0.6-0.7	34
0.7-0.8	9
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
0.7957	Intermediate Similarity	NPD1695	Approved
0.7917	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6371	Approved
0.7447	Intermediate Similarity	NPD4249	Approved
0.7368	Intermediate Similarity	NPD4250	Approved
0.7368	Intermediate Similarity	NPD4251	Approved
0.732	Intermediate Similarity	NPD5785	Approved
0.7156	Intermediate Similarity	NPD6053	Discontinued
0.7021	Intermediate Similarity	NPD6435	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5362	Discontinued
0.6827	Remote Similarity	NPD7638	Approved
0.6809	Remote Similarity	NPD4819	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6809	Remote Similarity	NPD4820	Approved
0.6809	Remote Similarity	NPD4821	Approved
0.6809	Remote Similarity	NPD4822	Approved
0.6804	Remote Similarity	NPD5363	Approved
0.6804	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.68	Remote Similarity	NPD46	Approved
0.68	Remote Similarity	NPD6698	Approved
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD4268	Approved
0.6771	Remote Similarity	NPD7154	Phase 3
0.6765	Remote Similarity	NPD5282	Discontinued
0.6762	Remote Similarity	NPD7640	Approved
0.6762	Remote Similarity	NPD7639	Approved
0.6737	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.6606	Remote Similarity	NPD6008	Approved
0.6566	Remote Similarity	NPD5786	Approved
0.6509	Remote Similarity	NPD4225	Approved
0.6505	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD7838	Discovery
0.6465	Remote Similarity	NPD1694	Approved
0.6458	Remote Similarity	NPD4252	Approved
0.6429	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD5331	Approved
0.6421	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD6083	Phase 2
0.6408	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD8035	Phase 2
0.6396	Remote Similarity	NPD5697	Approved
0.6396	Remote Similarity	NPD6412	Phase 2
0.6392	Remote Similarity	NPD4790	Discontinued
0.6381	Remote Similarity	NPD5695	Phase 3
0.6355	Remote Similarity	NPD5696	Approved
0.6348	Remote Similarity	NPD8133	Approved
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.6339	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.6327	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6649	Approved
0.6316	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD7507	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.6306	Remote Similarity	NPD5739	Approved
0.6283	Remote Similarity	NPD6014	Approved
0.6283	Remote Similarity	NPD6013	Approved
0.6283	Remote Similarity	NPD6372	Approved
0.6283	Remote Similarity	NPD6373	Approved
0.6283	Remote Similarity	NPD6012	Approved
0.6275	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD4788	Approved
0.625	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5701	Approved
0.6238	Remote Similarity	NPD7521	Approved
0.6238	Remote Similarity	NPD6409	Approved
0.6238	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD7146	Approved
0.6238	Remote Similarity	NPD6684	Approved
0.6238	Remote Similarity	NPD5330	Approved
0.623	Remote Similarity	NPD7492	Approved
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD3665	Phase 1
0.62	Remote Similarity	NPD3666	Approved
0.62	Remote Similarity	NPD3133	Approved
0.6195	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6179	Remote Similarity	NPD6616	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6174	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6174	Remote Similarity	NPD6617	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6163	Remote Similarity	NPD3198	Approved
0.616	Remote Similarity	NPD7319	Approved
0.614	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7078	Approved
0.6121	Remote Similarity	NPD6882	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6117	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6016	Approved
0.6116	Remote Similarity	NPD8033	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6095	Remote Similarity	NPD5284	Approved
0.6095	Remote Similarity	NPD5693	Phase 1
0.6095	Remote Similarity	NPD6411	Approved
0.6095	Remote Similarity	NPD5281	Approved
0.6091	Remote Similarity	NPD1700	Approved
0.6087	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4802	Phase 2
0.6082	Remote Similarity	NPD4238	Approved
0.608	Remote Similarity	NPD7736	Approved
0.6075	Remote Similarity	NPD5210	Approved
0.6075	Remote Similarity	NPD4629	Approved
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6370	Approved
0.6066	Remote Similarity	NPD5988	Approved
0.6058	Remote Similarity	NPD4753	Phase 2
0.6055	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6009	Approved
0.604	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5211	Phase 2
0.6033	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD5207	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6274	Approved
0.5965	Remote Similarity	NPD6685	Approved
0.5963	Remote Similarity	NPD4755	Approved
0.595	Remote Similarity	NPD7516	Approved
0.5946	Remote Similarity	NPD5344	Discontinued
0.5941	Remote Similarity	NPD6695	Phase 3
0.5929	Remote Similarity	NPD5141	Approved
0.5922	Remote Similarity	NPD3618	Phase 1
0.5905	Remote Similarity	NPD6101	Approved
0.5905	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8377	Approved
0.5902	Remote Similarity	NPD8294	Approved
0.5897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4633	Approved
0.5893	Remote Similarity	NPD5224	Approved
0.5893	Remote Similarity	NPD5225	Approved
0.5893	Remote Similarity	NPD5226	Approved
0.5891	Remote Similarity	NPD6845	Suspended
0.5888	Remote Similarity	NPD4202	Approved
0.5887	Remote Similarity	NPD7604	Phase 2
0.5882	Remote Similarity	NPD4786	Approved
0.5859	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4700	Approved
0.5854	Remote Similarity	NPD8380	Approved
0.5854	Remote Similarity	NPD8378	Approved
0.5854	Remote Similarity	NPD8296	Approved
0.5854	Remote Similarity	NPD8379	Approved
0.5854	Remote Similarity	NPD8335	Approved
0.5854	Remote Similarity	NPD7503	Approved
0.5841	Remote Similarity	NPD5174	Approved
0.5841	Remote Similarity	NPD5175	Approved
0.5833	Remote Similarity	NPD6001	Approved
0.5826	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7100	Approved
0.582	Remote Similarity	NPD7101	Approved
0.5818	Remote Similarity	NPD7902	Approved
0.5814	Remote Similarity	NPD7260	Phase 2
0.5812	Remote Similarity	NPD4634	Approved
0.581	Remote Similarity	NPD5737	Approved
0.581	Remote Similarity	NPD6672	Approved
0.5806	Remote Similarity	NPD229	Approved
0.5804	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD6336	Discontinued
0.5785	Remote Similarity	NPD6317	Approved
0.5773	Remote Similarity	NPD3702	Approved
0.5769	Remote Similarity	NPD5279	Phase 3
0.576	Remote Similarity	NPD6067	Discontinued
0.5758	Remote Similarity	NPD6115	Approved
0.5758	Remote Similarity	NPD6118	Approved
0.5758	Remote Similarity	NPD6114	Approved
0.5758	Remote Similarity	NPD6697	Approved
0.5755	Remote Similarity	NPD6904	Approved
0.5755	Remote Similarity	NPD6080	Approved
0.5755	Remote Similarity	NPD6051	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