NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	1.555
LogD:	2.226
LogS:	-2.358
# 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:	4.59
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:	-4.838
MDCK Permeability:	6.283099355641752e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.545

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.414
Plasma Protein Binding (PPB):	33.91328430175781%
Volume Distribution (VD):	0.636
Pgp-substrate:	53.90924072265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	13.688
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.64
Carcinogencity:	0.846
Eye Corrosion:	0.799
Eye Irritation:	0.188
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC155935

Natural Product ID:	NPC155935
*Common Name:**	Carabrolactone B
IUPAC Name:	(3aS,5R,5aS,8S,8aS,9S,9aS)-8,9-dihydroxy-5,8a-dimethyl-1-methylidene-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-2-one
Synonyms:	Carabrolactone B
Standard InCHIKey:	BKVXPJGDTWUKIM-FJBRTZCWSA-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/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9+,10+,11+,12-,13+,15+/m1/s1
SMILES:	C[C@@H]1C[C@H]2[C@@H](C(=C)C(=O)O2)[C@@H]([C@@]2(C)[C@H]1CC[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644105
PubChem CID:	53323205
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
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO23499	Carpesium faberi	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10.7	ug.mL-1	PMID[478537]

☑ 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 NPC155935 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	244
0.1-0.2	1747
0.2-0.3	6359
0.3-0.4	15215
0.4-0.5	8770
0.5-0.6	7042
0.6-0.7	2787
0.7-0.8	384
0.8-0.85	63
0.85-0.9	35
0.9-0.95	34
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC35809
0.9881	High Similarity	NPC54065
0.9881	High Similarity	NPC297474
0.9765	High Similarity	NPC293001
0.9765	High Similarity	NPC171360
0.9765	High Similarity	NPC29821
0.9765	High Similarity	NPC57304
0.9765	High Similarity	NPC35959
0.9765	High Similarity	NPC133888
0.9765	High Similarity	NPC63193
0.9639	High Similarity	NPC56593
0.9529	High Similarity	NPC215556
0.9419	High Similarity	NPC216284
0.9412	High Similarity	NPC217983
0.9412	High Similarity	NPC79549
0.9412	High Similarity	NPC207114
0.9405	High Similarity	NPC187661
0.9326	High Similarity	NPC18019
0.9326	High Similarity	NPC142529
0.9326	High Similarity	NPC91771
0.9326	High Similarity	NPC24956
0.9294	High Similarity	NPC24728
0.9222	High Similarity	NPC311904
0.9205	High Similarity	NPC200237
0.9195	High Similarity	NPC19087
0.9186	High Similarity	NPC471149
0.9167	High Similarity	NPC194859
0.9167	High Similarity	NPC224386
0.9101	High Similarity	NPC473331
0.9091	High Similarity	NPC184063
0.9091	High Similarity	NPC155215
0.908	High Similarity	NPC38392
0.908	High Similarity	NPC283409
0.9059	High Similarity	NPC284534
0.9059	High Similarity	NPC300082
0.9059	High Similarity	NPC204105
0.9048	High Similarity	NPC128246
0.9048	High Similarity	NPC111409
0.9	High Similarity	NPC472873
0.8989	High Similarity	NPC153590
0.8989	High Similarity	NPC258216
0.8989	High Similarity	NPC473273
0.8989	High Similarity	NPC473234
0.8989	High Similarity	NPC60386
0.8989	High Similarity	NPC473263
0.8989	High Similarity	NPC308656
0.8929	High Similarity	NPC246076
0.8925	High Similarity	NPC171759
0.8876	High Similarity	NPC286341
0.8876	High Similarity	NPC191339
0.8876	High Similarity	NPC475925
0.8864	High Similarity	NPC12872
0.8864	High Similarity	NPC168679
0.8851	High Similarity	NPC201658
0.8851	High Similarity	NPC118601
0.8824	High Similarity	NPC245665
0.881	High Similarity	NPC126248
0.8804	High Similarity	NPC471150
0.8791	High Similarity	NPC213698
0.8791	High Similarity	NPC170120
0.8791	High Similarity	NPC163228
0.8791	High Similarity	NPC476053
0.8791	High Similarity	NPC52044
0.875	High Similarity	NPC178875
0.8736	High Similarity	NPC309757
0.8736	High Similarity	NPC236692
0.8736	High Similarity	NPC304558
0.8681	High Similarity	NPC127019
0.8667	High Similarity	NPC131209
0.8652	High Similarity	NPC472872
0.8617	High Similarity	NPC471381
0.8602	High Similarity	NPC161493
0.8602	High Similarity	NPC474313
0.8602	High Similarity	NPC108475
0.8602	High Similarity	NPC170143
0.8602	High Similarity	NPC213947
0.8587	High Similarity	NPC67584
0.8523	High Similarity	NPC64153
0.8523	High Similarity	NPC67493
0.8523	High Similarity	NPC470242
0.8511	High Similarity	NPC45125
0.8495	Intermediate Similarity	NPC126156
0.8495	Intermediate Similarity	NPC213078
0.8478	Intermediate Similarity	NPC470010
0.8478	Intermediate Similarity	NPC198853
0.8478	Intermediate Similarity	NPC470013
0.8478	Intermediate Similarity	NPC262133
0.8478	Intermediate Similarity	NPC323008
0.8471	Intermediate Similarity	NPC258965
0.8471	Intermediate Similarity	NPC156658
0.8462	Intermediate Similarity	NPC133698
0.8427	Intermediate Similarity	NPC270270
0.8421	Intermediate Similarity	NPC186861
0.8404	Intermediate Similarity	NPC181151
0.8391	Intermediate Similarity	NPC54468
0.8372	Intermediate Similarity	NPC47635
0.8352	Intermediate Similarity	NPC301969
0.8352	Intermediate Similarity	NPC37607
0.8333	Intermediate Similarity	NPC224652
0.8333	Intermediate Similarity	NPC150923
0.8333	Intermediate Similarity	NPC91248
0.8316	Intermediate Similarity	NPC49833
0.8316	Intermediate Similarity	NPC249171
0.8316	Intermediate Similarity	NPC221615
0.8315	Intermediate Similarity	NPC238593
0.8295	Intermediate Similarity	NPC156485
0.828	Intermediate Similarity	NPC477131
0.8256	Intermediate Similarity	NPC293418
0.8256	Intermediate Similarity	NPC290508
0.8256	Intermediate Similarity	NPC73052
0.8256	Intermediate Similarity	NPC6823
0.8256	Intermediate Similarity	NPC51507
0.8229	Intermediate Similarity	NPC70865
0.8222	Intermediate Similarity	NPC190753
0.8211	Intermediate Similarity	NPC304445
0.8211	Intermediate Similarity	NPC236580
0.8202	Intermediate Similarity	NPC235792
0.8193	Intermediate Similarity	NPC320537
0.8193	Intermediate Similarity	NPC143979
0.8191	Intermediate Similarity	NPC304886
0.8182	Intermediate Similarity	NPC44004
0.8182	Intermediate Similarity	NPC54737
0.8172	Intermediate Similarity	NPC472874
0.8172	Intermediate Similarity	NPC135776
0.8172	Intermediate Similarity	NPC475788
0.8163	Intermediate Similarity	NPC221421
0.8163	Intermediate Similarity	NPC473148
0.8111	Intermediate Similarity	NPC162071
0.8085	Intermediate Similarity	NPC469596
0.8085	Intermediate Similarity	NPC148000
0.8085	Intermediate Similarity	NPC225474
0.8061	Intermediate Similarity	NPC80144
0.8043	Intermediate Similarity	NPC4986
0.8022	Intermediate Similarity	NPC186148
0.8021	Intermediate Similarity	NPC477949
0.802	Intermediate Similarity	NPC68248
0.8	Intermediate Similarity	NPC48803
0.8	Intermediate Similarity	NPC157686
0.8	Intermediate Similarity	NPC275960
0.8	Intermediate Similarity	NPC90121
0.8	Intermediate Similarity	NPC193645
0.8	Intermediate Similarity	NPC37408
0.8	Intermediate Similarity	NPC469873
0.8	Intermediate Similarity	NPC167893
0.8	Intermediate Similarity	NPC259042
0.7959	Intermediate Similarity	NPC67296
0.7957	Intermediate Similarity	NPC474323
0.7957	Intermediate Similarity	NPC206614
0.7941	Intermediate Similarity	NPC139838
0.7941	Intermediate Similarity	NPC59489
0.7935	Intermediate Similarity	NPC58219
0.7935	Intermediate Similarity	NPC177629
0.7917	Intermediate Similarity	NPC93245
0.7917	Intermediate Similarity	NPC476009
0.7917	Intermediate Similarity	NPC284518
0.7917	Intermediate Similarity	NPC474297
0.7907	Intermediate Similarity	NPC208223
0.7905	Intermediate Similarity	NPC471382
0.7905	Intermediate Similarity	NPC471380
0.79	Intermediate Similarity	NPC203659
0.7895	Intermediate Similarity	NPC24861
0.7879	Intermediate Similarity	NPC86077
0.7879	Intermediate Similarity	NPC225353
0.7865	Intermediate Similarity	NPC89555
0.7849	Intermediate Similarity	NPC32922
0.7849	Intermediate Similarity	NPC212664
0.7849	Intermediate Similarity	NPC116620
0.7849	Intermediate Similarity	NPC92974
0.7835	Intermediate Similarity	NPC263674
0.7835	Intermediate Similarity	NPC169205
0.7835	Intermediate Similarity	NPC261372
0.7835	Intermediate Similarity	NPC473963
0.7835	Intermediate Similarity	NPC58267
0.7822	Intermediate Similarity	NPC243998
0.7812	Intermediate Similarity	NPC224689
0.7812	Intermediate Similarity	NPC475900
0.7802	Intermediate Similarity	NPC165162
0.78	Intermediate Similarity	NPC474775
0.78	Intermediate Similarity	NPC124881
0.78	Intermediate Similarity	NPC110989
0.7778	Intermediate Similarity	NPC477950
0.7767	Intermediate Similarity	NPC115352
0.7766	Intermediate Similarity	NPC469368
0.7766	Intermediate Similarity	NPC129419
0.7766	Intermediate Similarity	NPC246173
0.7755	Intermediate Similarity	NPC216478
0.7755	Intermediate Similarity	NPC141191
0.7745	Intermediate Similarity	NPC26617
0.7742	Intermediate Similarity	NPC202672
0.7736	Intermediate Similarity	NPC123117
0.7732	Intermediate Similarity	NPC228766
0.7732	Intermediate Similarity	NPC165528
0.7732	Intermediate Similarity	NPC185553
0.7732	Intermediate Similarity	NPC473964
0.7727	Intermediate Similarity	NPC19841
0.7727	Intermediate Similarity	NPC470244
0.7727	Intermediate Similarity	NPC470239
0.7727	Intermediate Similarity	NPC182550
0.7717	Intermediate Similarity	NPC85698
0.7717	Intermediate Similarity	NPC474949

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 NPC155935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	2486
0.2-0.3	3892
0.3-0.4	1718
0.4-0.5	429
0.5-0.6	285
0.6-0.7	38
0.7-0.8	10
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
0.8043	Intermediate Similarity	NPD1695	Approved
0.8	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6371	Approved
0.7396	Intermediate Similarity	NPD5785	Approved
0.734	Intermediate Similarity	NPD4249	Approved
0.7263	Intermediate Similarity	NPD4251	Approved
0.7263	Intermediate Similarity	NPD4250	Approved
0.7064	Intermediate Similarity	NPD6053	Discontinued
0.7053	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5362	Discontinued
0.6915	Remote Similarity	NPD6435	Approved
0.6893	Remote Similarity	NPD7638	Approved
0.6882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5363	Approved
0.6875	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6698	Approved
0.6869	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD5282	Discontinued
0.6827	Remote Similarity	NPD7640	Approved
0.6827	Remote Similarity	NPD7639	Approved
0.6809	Remote Similarity	NPD5369	Approved
0.6737	Remote Similarity	NPD4269	Approved
0.6737	Remote Similarity	NPD4270	Approved
0.6702	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD4821	Approved
0.6702	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD5368	Approved
0.6702	Remote Similarity	NPD4822	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6633	Remote Similarity	NPD5786	Approved
0.6571	Remote Similarity	NPD4225	Approved
0.6569	Remote Similarity	NPD6399	Phase 3
0.6535	Remote Similarity	NPD7838	Discovery
0.6531	Remote Similarity	NPD1694	Approved
0.6526	Remote Similarity	NPD4252	Approved
0.6495	Remote Similarity	NPD5331	Approved
0.6495	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6083	Phase 2
0.6476	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD8035	Phase 2
0.6458	Remote Similarity	NPD4790	Discontinued
0.6455	Remote Similarity	NPD6412	Phase 2
0.6455	Remote Similarity	NPD5697	Approved
0.6442	Remote Similarity	NPD5695	Phase 3
0.6415	Remote Similarity	NPD5696	Approved
0.6404	Remote Similarity	NPD8133	Approved
0.6396	Remote Similarity	NPD6899	Approved
0.6396	Remote Similarity	NPD7320	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6392	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7632	Discontinued
0.6372	Remote Similarity	NPD6649	Approved
0.6372	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6364	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD6014	Approved
0.6339	Remote Similarity	NPD6012	Approved
0.6339	Remote Similarity	NPD6373	Approved
0.6339	Remote Similarity	NPD6372	Approved
0.6339	Remote Similarity	NPD6013	Approved
0.6337	Remote Similarity	NPD6903	Approved
0.6327	Remote Similarity	NPD4788	Approved
0.6311	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD7637	Suspended
0.6306	Remote Similarity	NPD5701	Approved
0.63	Remote Similarity	NPD7146	Approved
0.63	Remote Similarity	NPD6409	Approved
0.63	Remote Similarity	NPD7334	Approved
0.63	Remote Similarity	NPD7521	Approved
0.63	Remote Similarity	NPD5330	Approved
0.63	Remote Similarity	NPD6684	Approved
0.6283	Remote Similarity	NPD7290	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.6263	Remote Similarity	NPD3133	Approved
0.6263	Remote Similarity	NPD3666	Approved
0.6263	Remote Similarity	NPD3665	Phase 1
0.6261	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6239	Remote Similarity	NPD7115	Discovery
0.6235	Remote Similarity	NPD3198	Approved
0.623	Remote Similarity	NPD6616	Approved
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD6847	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6218	Remote Similarity	NPD6319	Approved
0.621	Remote Similarity	NPD7319	Approved
0.62	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7078	Approved
0.6176	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6882	Approved
0.6174	Remote Similarity	NPD8297	Approved
0.6167	Remote Similarity	NPD6015	Approved
0.6167	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6146	Remote Similarity	NPD4802	Phase 2
0.6146	Remote Similarity	NPD4238	Approved
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4629	Approved
0.6132	Remote Similarity	NPD5210	Approved
0.6129	Remote Similarity	NPD7736	Approved
0.6117	Remote Similarity	NPD4753	Phase 2
0.6116	Remote Similarity	NPD6370	Approved
0.6116	Remote Similarity	NPD5988	Approved
0.6111	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6009	Approved
0.61	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5211	Phase 2
0.6083	Remote Similarity	NPD6059	Approved
0.6061	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD3667	Approved
0.6058	Remote Similarity	NPD5207	Approved
0.6055	Remote Similarity	NPD5286	Approved
0.6055	Remote Similarity	NPD5285	Approved
0.6055	Remote Similarity	NPD4696	Approved
0.605	Remote Similarity	NPD7327	Approved
0.605	Remote Similarity	NPD7328	Approved
0.6048	Remote Similarity	NPD8293	Discontinued
0.6033	Remote Similarity	NPD5983	Phase 2
0.6033	Remote Similarity	NPD8033	Approved
0.6033	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4755	Approved
0.6017	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD1700	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD5344	Discontinued
0.5982	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5141	Approved
0.5982	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3618	Phase 1
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8294	Approved
0.595	Remote Similarity	NPD8377	Approved
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4633	Approved
0.5946	Remote Similarity	NPD5224	Approved
0.5946	Remote Similarity	NPD5225	Approved
0.5946	Remote Similarity	NPD5226	Approved
0.5943	Remote Similarity	NPD4202	Approved
0.5941	Remote Similarity	NPD4786	Approved
0.5938	Remote Similarity	NPD6845	Suspended
0.5935	Remote Similarity	NPD7604	Phase 2
0.5909	Remote Similarity	NPD4700	Approved
0.5902	Remote Similarity	NPD7503	Approved
0.5902	Remote Similarity	NPD8380	Approved
0.5902	Remote Similarity	NPD8296	Approved
0.5902	Remote Similarity	NPD8379	Approved
0.5902	Remote Similarity	NPD8378	Approved
0.5902	Remote Similarity	NPD8335	Approved
0.5893	Remote Similarity	NPD5175	Approved
0.5893	Remote Similarity	NPD5174	Approved
0.5888	Remote Similarity	NPD6001	Approved
0.5877	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6685	Approved
0.5872	Remote Similarity	NPD7902	Approved
0.587	Remote Similarity	NPD229	Approved
0.5868	Remote Similarity	NPD7101	Approved
0.5868	Remote Similarity	NPD7100	Approved
0.5865	Remote Similarity	NPD6672	Approved
0.5865	Remote Similarity	NPD5737	Approved
0.5862	Remote Similarity	NPD4634	Approved
0.5859	Remote Similarity	NPD7260	Phase 2
0.5856	Remote Similarity	NPD5223	Approved
0.584	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD3702	Approved
0.5833	Remote Similarity	NPD6317	Approved
0.5825	Remote Similarity	NPD5279	Phase 3
0.5816	Remote Similarity	NPD6118	Approved
0.5816	Remote Similarity	NPD6114	Approved
0.5816	Remote Similarity	NPD6115	Approved
0.5816	Remote Similarity	NPD6697	Approved
0.581	Remote Similarity	NPD6673	Approved
0.581	Remote Similarity	NPD6080	Approved
0.581	Remote Similarity	NPD6904	Approved
0.581	Remote Similarity	NPD6051	Approved
0.5806	Remote Similarity	NPD6067	Discontinued

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