NPASS Compound

Structure

NPC473273 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 1.7318 -2.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9388 0.8177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4060 0.8742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3388 -3.2880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4418 -1.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2046 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1392 -1.6877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9924 1.1409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 -0.8876 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1747 0.5653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3460 -3.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3746 1.1651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6977 2.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2319 2.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0470 -4.3269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2975 2.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6979 -0.7162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2538 -2.6072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 10 2 0 0 0 0 3 17 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 6 1 1 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 17 1 1 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 6 0 0 0 18 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.16
Volume:	336.41
LogP:	1.247
LogD:	1.261
LogS:	-3.494
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	4.557
Fsp3:	0.722
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:	-4.818
MDCK Permeability:	2.116437281074468e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.755

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.779
Plasma Protein Binding (PPB):	39.52910232543945%
Volume Distribution (VD):	0.525
Pgp-substrate:	64.57937622070312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.147
CYP1A2-substrate:	0.466
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.192
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	7.229
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.667
Carcinogencity:	0.485
Eye Corrosion:	0.019
Eye Irritation:	0.07
Respiratory Toxicity:	0.637

Download Data

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

Natural Product: NPC473273

Natural Product ID:	NPC473273
*Common Name:**	Chiapin B
IUPAC Name:	[(3aS,6aR,9aS,9bR)-6a-hydroxy-9a-methyl-3-methylidene-2,9-dioxo-4,5,6,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl propanoate
Synonyms:
Standard InCHIKey:	VNEOIQPRCFAFBK-KKTJJFPLSA-N
Standard InCHI:	InChI=1S/C18H24O6/c1-4-14(20)23-9-11-5-6-12-10(2)16(21)24-15(12)17(3)13(19)7-8-18(11,17)22/h11-12,15,22H,2,4-9H2,1,3H3/t11?,12-,15+,17-,18+/m0/s1
SMILES:	CCC(=O)OCC1CC[C@@H]2[C@H]([C@]3([C@@]1(O)CCC3=O)C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389845
PubChem CID:	44421651
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
NPO33481	parthenium hispitum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291045]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	26.0	%	PMID[570244]

☑ 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 NPC473273 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	255
0.1-0.2	1867
0.2-0.3	6545
0.3-0.4	13675
0.4-0.5	9865
0.5-0.6	6722
0.6-0.7	3176
0.7-0.8	461
0.8-0.85	62
0.85-0.9	33
0.9-0.95	27
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473234
1.0	High Similarity	NPC60386
1.0	High Similarity	NPC308656
1.0	High Similarity	NPC473263
0.9556	High Similarity	NPC213947
0.9556	High Similarity	NPC108475
0.9556	High Similarity	NPC170143
0.9545	High Similarity	NPC153590
0.9444	High Similarity	NPC142529
0.9444	High Similarity	NPC91771
0.9419	High Similarity	NPC201658
0.9326	High Similarity	NPC200237
0.9213	High Similarity	NPC286341
0.9213	High Similarity	NPC191339
0.913	High Similarity	NPC311904
0.9101	High Similarity	NPC54065
0.9101	High Similarity	NPC297474
0.9043	High Similarity	NPC171759
0.9011	High Similarity	NPC473331
0.9	High Similarity	NPC171360
0.9	High Similarity	NPC35959
0.9	High Similarity	NPC133888
0.9	High Similarity	NPC29821
0.9	High Similarity	NPC184063
0.9	High Similarity	NPC293001
0.9	High Similarity	NPC57304
0.9	High Similarity	NPC63193
0.8989	High Similarity	NPC12872
0.8989	High Similarity	NPC155935
0.8989	High Similarity	NPC168679
0.8977	High Similarity	NPC118601
0.8913	High Similarity	NPC163228
0.8889	High Similarity	NPC35809
0.8889	High Similarity	NPC19087
0.8876	High Similarity	NPC178875
0.8876	High Similarity	NPC79549
0.8864	High Similarity	NPC238593
0.8864	High Similarity	NPC56593
0.8778	High Similarity	NPC38392
0.8778	High Similarity	NPC215556
0.8764	High Similarity	NPC24728
0.875	High Similarity	NPC204105
0.875	High Similarity	NPC284534
0.875	High Similarity	NPC300082
0.871	High Similarity	NPC476053
0.8681	High Similarity	NPC216284
0.8667	High Similarity	NPC207114
0.8667	High Similarity	NPC471149
0.8667	High Similarity	NPC217983
0.8652	High Similarity	NPC304558
0.8617	High Similarity	NPC18019
0.8617	High Similarity	NPC24956
0.8617	High Similarity	NPC126156
0.8605	High Similarity	NPC6823
0.8587	High Similarity	NPC155215
0.8571	High Similarity	NPC283409
0.8526	High Similarity	NPC474313
0.8526	High Similarity	NPC471150
0.8523	High Similarity	NPC245665
0.8523	High Similarity	NPC54468
0.8511	High Similarity	NPC475900
0.8511	High Similarity	NPC472873
0.8495	Intermediate Similarity	NPC258216
0.8444	Intermediate Similarity	NPC187661
0.8444	Intermediate Similarity	NPC67493
0.8444	Intermediate Similarity	NPC236692
0.8444	Intermediate Similarity	NPC309757
0.8421	Intermediate Similarity	NPC476009
0.8409	Intermediate Similarity	NPC246076
0.8404	Intermediate Similarity	NPC127019
0.8391	Intermediate Similarity	NPC290508
0.8391	Intermediate Similarity	NPC73052
0.8391	Intermediate Similarity	NPC293418
0.8387	Intermediate Similarity	NPC133698
0.837	Intermediate Similarity	NPC472872
0.8352	Intermediate Similarity	NPC190753
0.8351	Intermediate Similarity	NPC186861
0.8333	Intermediate Similarity	NPC235792
0.8316	Intermediate Similarity	NPC67584
0.8316	Intermediate Similarity	NPC213698
0.8298	Intermediate Similarity	NPC135776
0.8295	Intermediate Similarity	NPC47635
0.8242	Intermediate Similarity	NPC470242
0.8229	Intermediate Similarity	NPC213078
0.8222	Intermediate Similarity	NPC224386
0.8222	Intermediate Similarity	NPC156485
0.8222	Intermediate Similarity	NPC194859
0.8211	Intermediate Similarity	NPC167219
0.8211	Intermediate Similarity	NPC198853
0.8211	Intermediate Similarity	NPC477131
0.82	Intermediate Similarity	NPC203659
0.8191	Intermediate Similarity	NPC131209
0.8191	Intermediate Similarity	NPC475925
0.8182	Intermediate Similarity	NPC156658
0.8182	Intermediate Similarity	NPC258965
0.8182	Intermediate Similarity	NPC225353
0.8163	Intermediate Similarity	NPC471381
0.8152	Intermediate Similarity	NPC270270
0.8144	Intermediate Similarity	NPC477949
0.8144	Intermediate Similarity	NPC169205
0.8144	Intermediate Similarity	NPC161493
0.8125	Intermediate Similarity	NPC275960
0.8125	Intermediate Similarity	NPC170120
0.8125	Intermediate Similarity	NPC48803
0.8125	Intermediate Similarity	NPC90121
0.8125	Intermediate Similarity	NPC52044
0.8125	Intermediate Similarity	NPC193645
0.8119	Intermediate Similarity	NPC44004
0.8111	Intermediate Similarity	NPC128246
0.8111	Intermediate Similarity	NPC111409
0.8105	Intermediate Similarity	NPC475788
0.81	Intermediate Similarity	NPC110989
0.8085	Intermediate Similarity	NPC301969
0.8085	Intermediate Similarity	NPC37607
0.8081	Intermediate Similarity	NPC474742
0.8081	Intermediate Similarity	NPC477950
0.8065	Intermediate Similarity	NPC91248
0.8065	Intermediate Similarity	NPC53158
0.8061	Intermediate Similarity	NPC45125
0.8061	Intermediate Similarity	NPC141191
0.8046	Intermediate Similarity	NPC208223
0.8043	Intermediate Similarity	NPC162071
0.8043	Intermediate Similarity	NPC64153
0.8041	Intermediate Similarity	NPC185553
0.8021	Intermediate Similarity	NPC262133
0.8021	Intermediate Similarity	NPC470013
0.8021	Intermediate Similarity	NPC470010
0.8021	Intermediate Similarity	NPC323008
0.802	Intermediate Similarity	NPC100487
0.8	Intermediate Similarity	NPC150978
0.8	Intermediate Similarity	NPC474747
0.8	Intermediate Similarity	NPC123177
0.8	Intermediate Similarity	NPC70595
0.8	Intermediate Similarity	NPC74103
0.798	Intermediate Similarity	NPC280963
0.7979	Intermediate Similarity	NPC32922
0.7978	Intermediate Similarity	NPC51507
0.7961	Intermediate Similarity	NPC255082
0.7959	Intermediate Similarity	NPC181151
0.7957	Intermediate Similarity	NPC186148
0.7941	Intermediate Similarity	NPC54737
0.7938	Intermediate Similarity	NPC304886
0.7921	Intermediate Similarity	NPC475945
0.7921	Intermediate Similarity	NPC475873
0.7921	Intermediate Similarity	NPC475871
0.7917	Intermediate Similarity	NPC472874
0.7912	Intermediate Similarity	NPC215294
0.7907	Intermediate Similarity	NPC320537
0.7907	Intermediate Similarity	NPC143979
0.79	Intermediate Similarity	NPC150923
0.79	Intermediate Similarity	NPC475099
0.7895	Intermediate Similarity	NPC71533
0.7895	Intermediate Similarity	NPC106510
0.7895	Intermediate Similarity	NPC253144
0.7889	Intermediate Similarity	NPC126248
0.7879	Intermediate Similarity	NPC221615
0.7872	Intermediate Similarity	NPC224652
0.7872	Intermediate Similarity	NPC58219
0.7872	Intermediate Similarity	NPC177629
0.7865	Intermediate Similarity	NPC19841
0.7864	Intermediate Similarity	NPC26617
0.7857	Intermediate Similarity	NPC39859
0.7857	Intermediate Similarity	NPC76862
0.7857	Intermediate Similarity	NPC158416
0.7857	Intermediate Similarity	NPC470883
0.7843	Intermediate Similarity	NPC474741
0.7812	Intermediate Similarity	NPC472705
0.7812	Intermediate Similarity	NPC261607
0.7812	Intermediate Similarity	NPC284185
0.7812	Intermediate Similarity	NPC300312
0.7812	Intermediate Similarity	NPC111114
0.781	Intermediate Similarity	NPC471884
0.781	Intermediate Similarity	NPC477103
0.7789	Intermediate Similarity	NPC92974
0.7789	Intermediate Similarity	NPC173926
0.7789	Intermediate Similarity	NPC474951
0.7767	Intermediate Similarity	NPC223450
0.7767	Intermediate Similarity	NPC243998
0.7757	Intermediate Similarity	NPC209058
0.7755	Intermediate Similarity	NPC469873
0.7745	Intermediate Similarity	NPC221421
0.7742	Intermediate Similarity	NPC21471
0.7742	Intermediate Similarity	NPC329749
0.7742	Intermediate Similarity	NPC33570
0.7723	Intermediate Similarity	NPC116139
0.7717	Intermediate Similarity	NPC318468
0.7717	Intermediate Similarity	NPC128429
0.7714	Intermediate Similarity	NPC59489
0.7714	Intermediate Similarity	NPC139838
0.7714	Intermediate Similarity	NPC477102
0.7708	Intermediate Similarity	NPC206614
0.7708	Intermediate Similarity	NPC246173
0.7708	Intermediate Similarity	NPC474323
0.77	Intermediate Similarity	NPC249171
0.77	Intermediate Similarity	NPC49833
0.7684	Intermediate Similarity	NPC202672
0.7677	Intermediate Similarity	NPC473964
0.767	Intermediate Similarity	NPC309190
0.766	Intermediate Similarity	NPC469676
0.766	Intermediate Similarity	NPC475019

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 NPC473273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	2583
0.2-0.3	3833
0.3-0.4	1655
0.4-0.5	436
0.5-0.6	272
0.6-0.7	54
0.7-0.8	6
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
0.8125	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6371	Approved
0.7604	Intermediate Similarity	NPD1695	Approved
0.7526	Intermediate Similarity	NPD5785	Approved
0.73	Intermediate Similarity	NPD5282	Discontinued
0.7128	Intermediate Similarity	NPD5369	Approved
0.701	Intermediate Similarity	NPD5363	Approved
0.701	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5786	Approved
0.6875	Remote Similarity	NPD4270	Approved
0.6875	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD4269	Approved
0.6789	Remote Similarity	NPD6008	Approved
0.6768	Remote Similarity	NPD4249	Approved
0.6701	Remote Similarity	NPD6435	Approved
0.67	Remote Similarity	NPD4251	Approved
0.67	Remote Similarity	NPD4250	Approved
0.6698	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6638	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD5362	Discontinued
0.6571	Remote Similarity	NPD5695	Phase 3
0.6542	Remote Similarity	NPD5696	Approved
0.6542	Remote Similarity	NPD7638	Approved
0.6538	Remote Similarity	NPD6399	Phase 3
0.6538	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD5779	Approved
0.6531	Remote Similarity	NPD5209	Approved
0.6529	Remote Similarity	NPD7492	Approved
0.6518	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6698	Approved
0.6505	Remote Similarity	NPD46	Approved
0.65	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1694	Approved
0.6495	Remote Similarity	NPD5368	Approved
0.6481	Remote Similarity	NPD7640	Approved
0.6481	Remote Similarity	NPD7639	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD6319	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6458	Remote Similarity	NPD4802	Phase 2
0.6458	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4238	Approved
0.6449	Remote Similarity	NPD6083	Phase 2
0.6449	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD6411	Approved
0.6442	Remote Similarity	NPD7637	Suspended
0.6442	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6372	Remote Similarity	NPD6881	Approved
0.6372	Remote Similarity	NPD6686	Approved
0.6372	Remote Similarity	NPD6899	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6649	Approved
0.6348	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6675	Approved
0.6339	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD6402	Approved
0.6339	Remote Similarity	NPD7128	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.6327	Remote Similarity	NPD4820	Approved
0.6327	Remote Similarity	NPD4819	Approved
0.6327	Remote Similarity	NPD4821	Approved
0.6327	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4822	Approved
0.632	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.6311	Remote Similarity	NPD6903	Approved
0.63	Remote Similarity	NPD4788	Approved
0.63	Remote Similarity	NPD7154	Phase 3
0.629	Remote Similarity	NPD8293	Discontinued
0.6286	Remote Similarity	NPD5693	Phase 1
0.6286	Remote Similarity	NPD8035	Phase 2
0.6286	Remote Similarity	NPD8034	Phase 2
0.6283	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD7146	Approved
0.6275	Remote Similarity	NPD6409	Approved
0.6275	Remote Similarity	NPD5330	Approved
0.6275	Remote Similarity	NPD7521	Approved
0.6275	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6684	Approved
0.6275	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD6883	Approved
0.6261	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4632	Approved
0.6228	Remote Similarity	NPD6011	Approved
0.621	Remote Similarity	NPD7507	Approved
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD5207	Approved
0.619	Remote Similarity	NPD7838	Discovery
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6882	Approved
0.614	Remote Similarity	NPD6412	Phase 2
0.6139	Remote Similarity	NPD5331	Approved
0.6139	Remote Similarity	NPD5332	Approved
0.6132	Remote Similarity	NPD5284	Approved
0.6132	Remote Similarity	NPD5281	Approved
0.6126	Remote Similarity	NPD1700	Approved
0.6122	Remote Similarity	NPD4268	Approved
0.6122	Remote Similarity	NPD4271	Approved
0.6121	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4634	Approved
0.6111	Remote Similarity	NPD5210	Approved
0.6111	Remote Similarity	NPD4629	Approved
0.6106	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8133	Approved
0.61	Remote Similarity	NPD4790	Discontinued
0.6095	Remote Similarity	NPD4753	Phase 2
0.6083	Remote Similarity	NPD6009	Approved
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6071	Remote Similarity	NPD5211	Phase 2
0.6071	Remote Similarity	NPD7632	Discontinued
0.6068	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7839	Suspended
0.6047	Remote Similarity	NPD6845	Suspended
0.604	Remote Similarity	NPD3667	Approved
0.6036	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD5285	Approved
0.6036	Remote Similarity	NPD5286	Approved
0.6034	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6001	Approved
0.6019	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8266	Approved
0.6016	Remote Similarity	NPD8267	Approved
0.6016	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8516	Approved
0.6016	Remote Similarity	NPD8268	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6016	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD4755	Approved
0.598	Remote Similarity	NPD6695	Phase 3
0.5979	Remote Similarity	NPD3702	Approved
0.5969	Remote Similarity	NPD7260	Phase 2
0.5965	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD3618	Phase 1
0.5946	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6904	Approved
0.5943	Remote Similarity	NPD6673	Approved
0.5943	Remote Similarity	NPD6080	Approved
0.5943	Remote Similarity	NPD5370	Suspended
0.5932	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5226	Approved
0.5929	Remote Similarity	NPD5224	Approved
0.5929	Remote Similarity	NPD5225	Approved
0.5929	Remote Similarity	NPD4633	Approved
0.5922	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4786	Approved
0.592	Remote Similarity	NPD7604	Phase 2
0.5893	Remote Similarity	NPD4700	Approved
0.5891	Remote Similarity	NPD5956	Approved
0.5888	Remote Similarity	NPD5692	Phase 3
0.5887	Remote Similarity	NPD6921	Approved
0.5882	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD4223	Phase 3
0.5877	Remote Similarity	NPD5175	Approved
0.5877	Remote Similarity	NPD5174	Approved
0.5872	Remote Similarity	NPD7748	Approved
0.5862	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6033	Approved
0.5856	Remote Similarity	NPD7902	Approved
0.5854	Remote Similarity	NPD7100	Approved
0.5854	Remote Similarity	NPD7101	Approved
0.5851	Remote Similarity	NPD229	Approved
0.5849	Remote Similarity	NPD5208	Approved
0.5843	Remote Similarity	NPD3198	Approved
0.5841	Remote Similarity	NPD5344	Discontinued
0.5841	Remote Similarity	NPD5223	Approved
0.5833	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD6079	Approved
0.5833	Remote Similarity	NPD6050	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