NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	1.636
LogD:	1.83
LogS:	-2.292
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	4.499
Fsp3:	0.867
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:	-4.647
MDCK Permeability:	5.1485811127349734e-05
Pgp-inhibitor:	0.899
Pgp-substrate:	0.181
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.747
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	36.58452224731445%
Volume Distribution (VD):	0.713
Pgp-substrate:	59.82133865356445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.286
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.259
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	12.55
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.304
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.557
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.379
Carcinogencity:	0.479
Eye Corrosion:	0.188
Eye Irritation:	0.27
Respiratory Toxicity:	0.634

Download Data

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

Natural Product: NPC179922

Natural Product ID:	NPC179922
*Common Name:**	11Beta,13-Dihydrocarpesiolin
IUPAC Name:	(1R,3aS,5R,5aS,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,7-b]furan-2,8-dione
Synonyms:	11Beta,13-Dihydrocarpesiolin
Standard InCHIKey:	LWZYMGJOEZRREO-WGOPJJQISA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h7-10,12-13,17H,4-6H2,1-3H3/t7-,8-,9+,10+,12-,13+,15+/m1/s1
SMILES:	C[C@@H]1C[C@H]2[C@@H]([C@@H](C)C(=O)O2)[C@@H]([C@@]2(C)[C@H]1CCC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911135
PubChem CID:	54671717
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

*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
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[21894898]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	19800.0	nM	PMID[469161]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20300.0	nM	PMID[469162]

☑ 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 NPC179922 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	493
0.1-0.2	4325
0.2-0.3	13135
0.3-0.4	11433
0.4-0.5	8142
0.5-0.6	4396
0.6-0.7	654
0.7-0.8	112
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC470243
0.8696	High Similarity	NPC157518
0.8514	High Similarity	NPC215030
0.8333	Intermediate Similarity	NPC51507
0.8313	Intermediate Similarity	NPC12872
0.8313	Intermediate Similarity	NPC168679
0.8267	Intermediate Similarity	NPC477867
0.8025	Intermediate Similarity	NPC157328
0.7917	Intermediate Similarity	NPC476330
0.7901	Intermediate Similarity	NPC212340
0.7882	Intermediate Similarity	NPC117405
0.7882	Intermediate Similarity	NPC52198
0.7778	Intermediate Similarity	NPC314103
0.7753	Intermediate Similarity	NPC91771
0.7753	Intermediate Similarity	NPC142529
0.7753	Intermediate Similarity	NPC126156
0.7738	Intermediate Similarity	NPC236692
0.7738	Intermediate Similarity	NPC238593
0.7738	Intermediate Similarity	NPC309757
0.7674	Intermediate Similarity	NPC200580
0.7647	Intermediate Similarity	NPC201658
0.7619	Intermediate Similarity	NPC473350
0.7614	Intermediate Similarity	NPC153590
0.7614	Intermediate Similarity	NPC200237
0.76	Intermediate Similarity	NPC319007
0.7558	Intermediate Similarity	NPC53158
0.7528	Intermediate Similarity	NPC473331
0.7468	Intermediate Similarity	NPC132064
0.7467	Intermediate Similarity	NPC469925
0.7444	Intermediate Similarity	NPC193645
0.7444	Intermediate Similarity	NPC275960
0.7444	Intermediate Similarity	NPC48803
0.7444	Intermediate Similarity	NPC90121
0.7436	Intermediate Similarity	NPC474755
0.7419	Intermediate Similarity	NPC171759
0.7416	Intermediate Similarity	NPC473263
0.7416	Intermediate Similarity	NPC308656
0.7416	Intermediate Similarity	NPC60386
0.7416	Intermediate Similarity	NPC472238
0.7416	Intermediate Similarity	NPC472237
0.7416	Intermediate Similarity	NPC473273
0.7416	Intermediate Similarity	NPC473234
0.7381	Intermediate Similarity	NPC128246
0.7381	Intermediate Similarity	NPC111409
0.7381	Intermediate Similarity	NPC54468
0.7368	Intermediate Similarity	NPC119838
0.7363	Intermediate Similarity	NPC193785
0.7363	Intermediate Similarity	NPC185553
0.7356	Intermediate Similarity	NPC470009
0.7342	Intermediate Similarity	NPC125164
0.7333	Intermediate Similarity	NPC470424
0.7333	Intermediate Similarity	NPC289004
0.7326	Intermediate Similarity	NPC70422
0.7326	Intermediate Similarity	NPC104961
0.7326	Intermediate Similarity	NPC70555
0.7303	Intermediate Similarity	NPC191339
0.7303	Intermediate Similarity	NPC286341
0.7294	Intermediate Similarity	NPC477434
0.7284	Intermediate Similarity	NPC169389
0.7284	Intermediate Similarity	NPC83108
0.7284	Intermediate Similarity	NPC477918
0.7284	Intermediate Similarity	NPC214030
0.7284	Intermediate Similarity	NPC307865
0.7283	Intermediate Similarity	NPC169205
0.7283	Intermediate Similarity	NPC311904
0.7273	Intermediate Similarity	NPC155935
0.7273	Intermediate Similarity	NPC475062
0.7241	Intermediate Similarity	NPC118601
0.7234	Intermediate Similarity	NPC477950
0.7229	Intermediate Similarity	NPC290508
0.7229	Intermediate Similarity	NPC1882
0.7229	Intermediate Similarity	NPC73052
0.7229	Intermediate Similarity	NPC6823
0.7229	Intermediate Similarity	NPC293418
0.7222	Intermediate Similarity	NPC476189
0.7215	Intermediate Similarity	NPC475232
0.7215	Intermediate Similarity	NPC473775
0.7215	Intermediate Similarity	NPC475260
0.7215	Intermediate Similarity	NPC473699
0.7215	Intermediate Similarity	NPC51249
0.7215	Intermediate Similarity	NPC474100
0.7209	Intermediate Similarity	NPC478111
0.7204	Intermediate Similarity	NPC274695
0.7204	Intermediate Similarity	NPC141191
0.72	Intermediate Similarity	NPC306805
0.72	Intermediate Similarity	NPC215987
0.7195	Intermediate Similarity	NPC470014
0.7191	Intermediate Similarity	NPC54065
0.7191	Intermediate Similarity	NPC35809
0.7191	Intermediate Similarity	NPC297474
0.7191	Intermediate Similarity	NPC19087
0.7176	Intermediate Similarity	NPC472847
0.7176	Intermediate Similarity	NPC15091
0.716	Intermediate Similarity	NPC477933
0.716	Intermediate Similarity	NPC477932
0.7159	Intermediate Similarity	NPC178875
0.7143	Intermediate Similarity	NPC126248
0.7143	Intermediate Similarity	NPC206878
0.7126	Intermediate Similarity	NPC92139
0.7126	Intermediate Similarity	NPC476717
0.7113	Intermediate Similarity	NPC168890
0.7113	Intermediate Similarity	NPC41674
0.7113	Intermediate Similarity	NPC469441
0.7113	Intermediate Similarity	NPC228311
0.7111	Intermediate Similarity	NPC29821
0.7111	Intermediate Similarity	NPC293001
0.7111	Intermediate Similarity	NPC184063
0.7111	Intermediate Similarity	NPC63193
0.7111	Intermediate Similarity	NPC171360
0.7111	Intermediate Similarity	NPC57304
0.7111	Intermediate Similarity	NPC35959
0.7111	Intermediate Similarity	NPC474065
0.7111	Intermediate Similarity	NPC133888
0.7097	Intermediate Similarity	NPC170143
0.7097	Intermediate Similarity	NPC108475
0.7097	Intermediate Similarity	NPC213947
0.7093	Intermediate Similarity	NPC291310
0.7093	Intermediate Similarity	NPC165287
0.7079	Intermediate Similarity	NPC471459
0.7079	Intermediate Similarity	NPC61688
0.7079	Intermediate Similarity	NPC67653
0.7079	Intermediate Similarity	NPC38392
0.7079	Intermediate Similarity	NPC477440
0.7079	Intermediate Similarity	NPC477443
0.7073	Intermediate Similarity	NPC474003
0.7073	Intermediate Similarity	NPC70996
0.7065	Intermediate Similarity	NPC62407
0.7065	Intermediate Similarity	NPC287354
0.7051	Intermediate Similarity	NPC5714
0.7051	Intermediate Similarity	NPC98711
0.7045	Intermediate Similarity	NPC475773
0.7045	Intermediate Similarity	NPC239938
0.7041	Intermediate Similarity	NPC290247
0.7041	Intermediate Similarity	NPC176756
0.7041	Intermediate Similarity	NPC469787
0.7041	Intermediate Similarity	NPC469788
0.7037	Intermediate Similarity	NPC228411
0.7037	Intermediate Similarity	NPC35871
0.7037	Intermediate Similarity	NPC68565
0.7037	Intermediate Similarity	NPC477934
0.7033	Intermediate Similarity	NPC475788
0.7021	Intermediate Similarity	NPC253995
0.701	Intermediate Similarity	NPC473701
0.701	Intermediate Similarity	NPC473526
0.7	Intermediate Similarity	NPC477444
0.7	Intermediate Similarity	NPC477433
0.7	Intermediate Similarity	NPC248567
0.7	Intermediate Similarity	NPC253144
0.7	Intermediate Similarity	NPC477442
0.6988	Remote Similarity	NPC185465
0.6988	Remote Similarity	NPC475616
0.6986	Remote Similarity	NPC475821
0.6979	Remote Similarity	NPC225353
0.6974	Remote Similarity	NPC295256
0.697	Remote Similarity	NPC220773
0.697	Remote Similarity	NPC278693
0.697	Remote Similarity	NPC329876
0.697	Remote Similarity	NPC167044
0.6966	Remote Similarity	NPC217983
0.6966	Remote Similarity	NPC207114
0.6966	Remote Similarity	NPC477614
0.6966	Remote Similarity	NPC471221
0.6966	Remote Similarity	NPC226491
0.6957	Remote Similarity	NPC247877
0.6957	Remote Similarity	NPC309127
0.6951	Remote Similarity	NPC474020
0.6941	Remote Similarity	NPC58631
0.6941	Remote Similarity	NPC470241
0.6941	Remote Similarity	NPC475743
0.6933	Remote Similarity	NPC474552
0.6932	Remote Similarity	NPC120395
0.6932	Remote Similarity	NPC56593
0.6932	Remote Similarity	NPC187661
0.6923	Remote Similarity	NPC70595
0.6923	Remote Similarity	NPC123177
0.6923	Remote Similarity	NPC82315
0.6923	Remote Similarity	NPC284185
0.6923	Remote Similarity	NPC74103
0.6923	Remote Similarity	NPC474699
0.6923	Remote Similarity	NPC150978
0.6915	Remote Similarity	NPC278028
0.6915	Remote Similarity	NPC328180
0.6914	Remote Similarity	NPC317212
0.6914	Remote Similarity	NPC477930
0.6907	Remote Similarity	NPC110989
0.6905	Remote Similarity	NPC472310
0.6905	Remote Similarity	NPC474754
0.6905	Remote Similarity	NPC320144
0.69	Remote Similarity	NPC217041
0.6897	Remote Similarity	NPC319909
0.6897	Remote Similarity	NPC471044
0.6897	Remote Similarity	NPC473336
0.6892	Remote Similarity	NPC469921
0.6889	Remote Similarity	NPC212664
0.6889	Remote Similarity	NPC32922
0.6889	Remote Similarity	NPC215556
0.6882	Remote Similarity	NPC163228
0.6882	Remote Similarity	NPC470191
0.6867	Remote Similarity	NPC471151
0.6867	Remote Similarity	NPC208223

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 NPC179922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	679
0.1-0.2	4083
0.2-0.3	2957
0.3-0.4	823
0.4-0.5	418
0.5-0.6	172
0.6-0.7	15
0.7-0.8	3
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
0.7444	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD229	Approved
0.6988	Remote Similarity	NPD4802	Phase 2
0.6988	Remote Similarity	NPD4238	Approved
0.6986	Remote Similarity	NPD3198	Approved
0.6974	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6435	Approved
0.6761	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6116	Phase 1
0.6628	Remote Similarity	NPD5368	Approved
0.6627	Remote Similarity	NPD3702	Approved
0.6556	Remote Similarity	NPD5786	Approved
0.6552	Remote Similarity	NPD5369	Approved
0.6548	Remote Similarity	NPD6117	Approved
0.6538	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5777	Approved
0.6429	Remote Similarity	NPD3703	Phase 2
0.642	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3698	Phase 2
0.641	Remote Similarity	NPD7909	Approved
0.6395	Remote Similarity	NPD6115	Approved
0.6395	Remote Similarity	NPD6118	Approved
0.6395	Remote Similarity	NPD6114	Approved
0.6395	Remote Similarity	NPD6697	Approved
0.6341	Remote Similarity	NPD4244	Approved
0.6341	Remote Similarity	NPD4245	Approved
0.6301	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4269	Approved
0.6292	Remote Similarity	NPD4270	Approved
0.6277	Remote Similarity	NPD5785	Approved
0.6265	Remote Similarity	NPD6081	Approved
0.6265	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4224	Phase 2
0.6211	Remote Similarity	NPD6411	Approved
0.6207	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6399	Phase 3
0.6145	Remote Similarity	NPD4789	Approved
0.6143	Remote Similarity	NPD2266	Phase 2
0.6111	Remote Similarity	NPD9638	Phase 2
0.6087	Remote Similarity	NPD634	Phase 3
0.6087	Remote Similarity	NPD5363	Approved
0.6082	Remote Similarity	NPD5282	Discontinued
0.6081	Remote Similarity	NPD3728	Approved
0.6081	Remote Similarity	NPD3730	Approved
0.6067	Remote Similarity	NPD4252	Approved
0.6042	Remote Similarity	NPD8035	Phase 2
0.6042	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD6402	Approved
0.5962	Remote Similarity	NPD7128	Approved
0.5962	Remote Similarity	NPD6675	Approved
0.5962	Remote Similarity	NPD5739	Approved
0.5943	Remote Similarity	NPD6373	Approved
0.5943	Remote Similarity	NPD6372	Approved
0.5934	Remote Similarity	NPD7345	Approved
0.5921	Remote Similarity	NPD73	Approved
0.5905	Remote Similarity	NPD5701	Approved
0.5905	Remote Similarity	NPD5697	Approved
0.5905	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6371	Approved
0.587	Remote Similarity	NPD5362	Discontinued
0.5854	Remote Similarity	NPD375	Phase 2
0.5851	Remote Similarity	NPD4249	Approved
0.5849	Remote Similarity	NPD6899	Approved
0.5849	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6881	Approved
0.5843	Remote Similarity	NPD3671	Phase 1
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD6649	Approved
0.5833	Remote Similarity	NPD1695	Approved
0.5816	Remote Similarity	NPD5779	Approved
0.5816	Remote Similarity	NPD5778	Approved
0.5794	Remote Similarity	NPD6014	Approved
0.5794	Remote Similarity	NPD6013	Approved
0.5794	Remote Similarity	NPD6012	Approved
0.5789	Remote Similarity	NPD4251	Approved
0.5789	Remote Similarity	NPD4250	Approved
0.5745	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6084	Phase 2
0.5743	Remote Similarity	NPD6083	Phase 2
0.5741	Remote Similarity	NPD7290	Approved
0.5741	Remote Similarity	NPD7102	Approved
0.5741	Remote Similarity	NPD6883	Approved
0.5729	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD5360	Phase 3
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4821	Approved
0.5714	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6011	Approved
0.57	Remote Similarity	NPD5695	Phase 3
0.5699	Remote Similarity	NPD7154	Phase 3
0.5688	Remote Similarity	NPD6847	Approved
0.5688	Remote Similarity	NPD6869	Approved
0.5688	Remote Similarity	NPD6617	Approved
0.5688	Remote Similarity	NPD8130	Phase 1
0.5686	Remote Similarity	NPD5696	Approved
0.5673	Remote Similarity	NPD8086	Approved
0.5673	Remote Similarity	NPD8082	Approved
0.5673	Remote Similarity	NPD8139	Approved
0.5673	Remote Similarity	NPD8085	Approved
0.5673	Remote Similarity	NPD8138	Approved
0.5673	Remote Similarity	NPD8083	Approved
0.5673	Remote Similarity	NPD8084	Approved
0.5667	Remote Similarity	NPD4271	Approved
0.5667	Remote Similarity	NPD4268	Approved
0.566	Remote Similarity	NPD6008	Approved
0.5652	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7492	Approved
0.5641	Remote Similarity	NPD8959	Approved
0.5636	Remote Similarity	NPD6882	Approved
0.5636	Remote Similarity	NPD8297	Approved
0.5619	Remote Similarity	NPD8276	Approved
0.5619	Remote Similarity	NPD8275	Approved
0.5614	Remote Similarity	NPD7519	Approved
0.5614	Remote Similarity	NPD7517	Approved
0.5614	Remote Similarity	NPD7518	Approved
0.56	Remote Similarity	NPD72	Approved
0.56	Remote Similarity	NPD3186	Phase 1
0.56	Remote Similarity	NPD65	Approved
0.56	Remote Similarity	NPD8960	Approved
0.56	Remote Similarity	NPD9009	Approved
0.56	Remote Similarity	NPD66	Approved
0.56	Remote Similarity	NPD64	Approved
0.56	Remote Similarity	NPD9008	Approved
0.56	Remote Similarity	NPD9011	Approved
0.56	Remote Similarity	NPD9010	Approved
0.56	Remote Similarity	NPD9007	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