NPASS Compound

Structure

CID142529 OpenBabel06191715502D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.0533 1.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2704 -2.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0324 -1.2190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2648 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.6922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3600 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9960 -0.0896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2389 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8789 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2185 -1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2430 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1195 -1.4985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3930 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0204 -1.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9685 -2.5734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 -2.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 -1.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7518 0.8584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 8 2 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 1 1 6 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 5 1 6 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 1 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 8 1 1 0 0 0 12 14 1 0 0 0 0 13 16 1 1 0 0 0 14 16 1 6 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.15
Volume:	295.665
LogP:	1.067
LogD:	1.618
LogS:	-2.8
# Rotatable Bonds:	1
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	4.75
Fsp3:	0.75
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:	-4.689
MDCK Permeability:	3.558524986146949e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.718

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895
Plasma Protein Binding (PPB):	26.83637237548828%
Volume Distribution (VD):	0.611
Pgp-substrate:	60.30259704589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.638
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	9.664
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.681
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.615
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.671
Carcinogencity:	0.74
Eye Corrosion:	0.785
Eye Irritation:	0.616
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: NPC142529

Natural Product ID:	NPC142529
*Common Name:**	(1S,2R,5R,6S,7S,8S,10R)-6-Hydroxy-2-Methoxy-4-Oxopseudoguai-11(13)-En-12,8-Olide
IUPAC Name:	(3aS,5R,5aS,6R,8aR,9S,9aS)-9-hydroxy-6-methoxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
Synonyms:
Standard InCHIKey:	FAIKGOKPMORPNZ-HFOVEJHBSA-N
Standard InCHI:	InChI=1S/C16H22O5/c1-7-5-9-12(8(2)15(19)21-9)14(18)16(3)11(17)6-10(20-4)13(7)16/h7,9-10,12-14,18H,2,5-6H2,1,3-4H3/t7-,9+,10-,12-,13-,14+,16-/m1/s1
SMILES:	CO[C@@H]1CC(=O)[C@@]2([C@@H]1[C@H](C)C[C@H]1[C@H]([C@@H]2O)C(=C)C(=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911131
PubChem CID:	54671716
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]
NPO4280	Inula hupehensis	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5100.0	nM	PMID[518882]

☑ 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 NPC142529 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	278
0.1-0.2	1911
0.2-0.3	6514
0.3-0.4	13161
0.4-0.5	10067
0.5-0.6	6701
0.6-0.7	3374
0.7-0.8	557
0.8-0.85	60
0.85-0.9	31
0.9-0.95	37
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91771
0.9663	High Similarity	NPC200237
0.957	High Similarity	NPC171759
0.9551	High Similarity	NPC286341
0.9551	High Similarity	NPC191339
0.9444	High Similarity	NPC473273
0.9444	High Similarity	NPC153590
0.9444	High Similarity	NPC308656
0.9444	High Similarity	NPC473234
0.9444	High Similarity	NPC60386
0.9444	High Similarity	NPC473263
0.9438	High Similarity	NPC297474
0.9438	High Similarity	NPC54065
0.9341	High Similarity	NPC473331
0.9333	High Similarity	NPC63193
0.9333	High Similarity	NPC133888
0.9333	High Similarity	NPC293001
0.9333	High Similarity	NPC35959
0.9333	High Similarity	NPC29821
0.9333	High Similarity	NPC171360
0.9333	High Similarity	NPC57304
0.9326	High Similarity	NPC155935
0.9326	High Similarity	NPC168679
0.9326	High Similarity	NPC12872
0.9247	High Similarity	NPC311904
0.9222	High Similarity	NPC19087
0.9222	High Similarity	NPC35809
0.914	High Similarity	NPC126156
0.9121	High Similarity	NPC184063
0.9111	High Similarity	NPC38392
0.9043	High Similarity	NPC213947
0.9043	High Similarity	NPC170143
0.9043	High Similarity	NPC108475
0.9032	High Similarity	NPC163228
0.9	High Similarity	NPC217983
0.9	High Similarity	NPC207114
0.8989	High Similarity	NPC238593
0.8989	High Similarity	NPC56593
0.8936	High Similarity	NPC18019
0.8936	High Similarity	NPC24956
0.8901	High Similarity	NPC215556
0.8889	High Similarity	NPC201658
0.8889	High Similarity	NPC118601
0.8889	High Similarity	NPC24728
0.8842	High Similarity	NPC471150
0.883	High Similarity	NPC476053
0.8804	High Similarity	NPC216284
0.8791	High Similarity	NPC178875
0.8791	High Similarity	NPC471149
0.8791	High Similarity	NPC79549
0.8778	High Similarity	NPC309757
0.8778	High Similarity	NPC236692
0.8778	High Similarity	NPC187661
0.8778	High Similarity	NPC304558
0.8696	High Similarity	NPC283409
0.8652	High Similarity	NPC54468
0.8646	High Similarity	NPC474313
0.8632	High Similarity	NPC472873
0.8556	High Similarity	NPC224386
0.8556	High Similarity	NPC194859
0.8542	High Similarity	NPC476009
0.8539	High Similarity	NPC246076
0.8511	High Similarity	NPC155215
0.8511	High Similarity	NPC475925
0.85	High Similarity	NPC203659
0.8485	Intermediate Similarity	NPC225353
0.8469	Intermediate Similarity	NPC186861
0.8469	Intermediate Similarity	NPC471381
0.8462	Intermediate Similarity	NPC300082
0.8462	Intermediate Similarity	NPC204105
0.8462	Intermediate Similarity	NPC284534
0.8454	Intermediate Similarity	NPC169205
0.8444	Intermediate Similarity	NPC111409
0.8444	Intermediate Similarity	NPC128246
0.8438	Intermediate Similarity	NPC475900
0.8438	Intermediate Similarity	NPC48803
0.8438	Intermediate Similarity	NPC90121
0.8438	Intermediate Similarity	NPC275960
0.8438	Intermediate Similarity	NPC193645
0.8438	Intermediate Similarity	NPC213698
0.8421	Intermediate Similarity	NPC258216
0.84	Intermediate Similarity	NPC110989
0.8384	Intermediate Similarity	NPC477950
0.837	Intermediate Similarity	NPC470242
0.8367	Intermediate Similarity	NPC141191
0.8351	Intermediate Similarity	NPC185553
0.8333	Intermediate Similarity	NPC127019
0.8315	Intermediate Similarity	NPC73052
0.8315	Intermediate Similarity	NPC293418
0.8315	Intermediate Similarity	NPC6823
0.8315	Intermediate Similarity	NPC290508
0.8315	Intermediate Similarity	NPC51507
0.8298	Intermediate Similarity	NPC472872
0.828	Intermediate Similarity	NPC270270
0.8265	Intermediate Similarity	NPC161493
0.8265	Intermediate Similarity	NPC477949
0.8247	Intermediate Similarity	NPC52044
0.8247	Intermediate Similarity	NPC67584
0.8247	Intermediate Similarity	NPC170120
0.8242	Intermediate Similarity	NPC245665
0.8235	Intermediate Similarity	NPC44004
0.8235	Intermediate Similarity	NPC54737
0.8229	Intermediate Similarity	NPC475788
0.8229	Intermediate Similarity	NPC135776
0.8222	Intermediate Similarity	NPC126248
0.8172	Intermediate Similarity	NPC64153
0.8163	Intermediate Similarity	NPC213078
0.8144	Intermediate Similarity	NPC198853
0.8137	Intermediate Similarity	NPC100487
0.8125	Intermediate Similarity	NPC74103
0.8125	Intermediate Similarity	NPC150978
0.8125	Intermediate Similarity	NPC131209
0.8125	Intermediate Similarity	NPC70595
0.8125	Intermediate Similarity	NPC123177
0.8125	Intermediate Similarity	NPC133698
0.8119	Intermediate Similarity	NPC474747
0.8119	Intermediate Similarity	NPC80144
0.8085	Intermediate Similarity	NPC190753
0.8085	Intermediate Similarity	NPC186148
0.8039	Intermediate Similarity	NPC475945
0.8039	Intermediate Similarity	NPC475871
0.8039	Intermediate Similarity	NPC221421
0.8022	Intermediate Similarity	NPC47635
0.8021	Intermediate Similarity	NPC253144
0.8021	Intermediate Similarity	NPC246173
0.8021	Intermediate Similarity	NPC71533
0.8021	Intermediate Similarity	NPC106510
0.802	Intermediate Similarity	NPC150923
0.802	Intermediate Similarity	NPC67296
0.8	Intermediate Similarity	NPC249171
0.8	Intermediate Similarity	NPC177629
0.8	Intermediate Similarity	NPC45125
0.8	Intermediate Similarity	NPC58219
0.8	Intermediate Similarity	NPC49833
0.8	Intermediate Similarity	NPC59489
0.8	Intermediate Similarity	NPC139838
0.798	Intermediate Similarity	NPC39859
0.798	Intermediate Similarity	NPC76862
0.798	Intermediate Similarity	NPC158416
0.798	Intermediate Similarity	NPC470883
0.7979	Intermediate Similarity	NPC67493
0.7978	Intermediate Similarity	NPC208223
0.7963	Intermediate Similarity	NPC471382
0.7963	Intermediate Similarity	NPC471380
0.7959	Intermediate Similarity	NPC323008
0.7959	Intermediate Similarity	NPC477131
0.7959	Intermediate Similarity	NPC470013
0.7959	Intermediate Similarity	NPC470010
0.7959	Intermediate Similarity	NPC262133
0.7938	Intermediate Similarity	NPC221282
0.7938	Intermediate Similarity	NPC284185
0.7921	Intermediate Similarity	NPC280963
0.7917	Intermediate Similarity	NPC92974
0.7917	Intermediate Similarity	NPC52198
0.7917	Intermediate Similarity	NPC117405
0.7917	Intermediate Similarity	NPC32922
0.7912	Intermediate Similarity	NPC258965
0.7912	Intermediate Similarity	NPC156658
0.79	Intermediate Similarity	NPC181151
0.79	Intermediate Similarity	NPC304445
0.79	Intermediate Similarity	NPC236580
0.7885	Intermediate Similarity	NPC243998
0.7879	Intermediate Similarity	NPC469873
0.7879	Intermediate Similarity	NPC37408
0.7879	Intermediate Similarity	NPC304886
0.7872	Intermediate Similarity	NPC235792
0.787	Intermediate Similarity	NPC209058
0.7864	Intermediate Similarity	NPC473148
0.7864	Intermediate Similarity	NPC474775
0.7857	Intermediate Similarity	NPC472874
0.7843	Intermediate Similarity	NPC39683
0.7843	Intermediate Similarity	NPC475099
0.7843	Intermediate Similarity	NPC474742
0.7835	Intermediate Similarity	NPC37607
0.7835	Intermediate Similarity	NPC301969
0.7822	Intermediate Similarity	NPC221615
0.7812	Intermediate Similarity	NPC53158
0.7812	Intermediate Similarity	NPC91248
0.7812	Intermediate Similarity	NPC202672
0.7812	Intermediate Similarity	NPC224652
0.781	Intermediate Similarity	NPC26617
0.7802	Intermediate Similarity	NPC19841
0.7798	Intermediate Similarity	NPC123117
0.7789	Intermediate Similarity	NPC474949
0.7789	Intermediate Similarity	NPC475019
0.7789	Intermediate Similarity	NPC162071
0.7788	Intermediate Similarity	NPC474741
0.7788	Intermediate Similarity	NPC309190
0.7778	Intermediate Similarity	NPC190294
0.7778	Intermediate Similarity	NPC167219
0.7767	Intermediate Similarity	NPC164551
0.7766	Intermediate Similarity	NPC156485
0.7757	Intermediate Similarity	NPC477103
0.7757	Intermediate Similarity	NPC257240
0.7757	Intermediate Similarity	NPC471884
0.7755	Intermediate Similarity	NPC184463
0.7755	Intermediate Similarity	NPC208886
0.7755	Intermediate Similarity	NPC12172
0.7753	Intermediate Similarity	NPC179922
0.7748	Intermediate Similarity	NPC161060

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 NPC142529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	2631
0.2-0.3	3814
0.3-0.4	1609
0.4-0.5	421
0.5-0.6	255
0.6-0.7	85
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6371	Approved
0.7653	Intermediate Similarity	NPD5785	Approved
0.7551	Intermediate Similarity	NPD1695	Approved
0.7245	Intermediate Similarity	NPD5786	Approved
0.7188	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD5363	Approved
0.7087	Intermediate Similarity	NPD5282	Discontinued
0.7083	Intermediate Similarity	NPD5369	Approved
0.7071	Intermediate Similarity	NPD4249	Approved
0.701	Intermediate Similarity	NPD4270	Approved
0.701	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4250	Approved
0.7	Intermediate Similarity	NPD4251	Approved
0.6979	Remote Similarity	NPD5368	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.6804	Remote Similarity	NPD4252	Approved
0.68	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7492	Approved
0.6768	Remote Similarity	NPD5362	Discontinued
0.6731	Remote Similarity	NPD7983	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6723	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6637	Remote Similarity	NPD6881	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7320	Approved
0.6637	Remote Similarity	NPD6899	Approved
0.6635	Remote Similarity	NPD46	Approved
0.6635	Remote Similarity	NPD6698	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6649	Approved
0.6607	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6675	Approved
0.6607	Remote Similarity	NPD7128	Approved
0.6607	Remote Similarity	NPD6402	Approved
0.6606	Remote Similarity	NPD7640	Approved
0.6606	Remote Similarity	NPD7639	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6579	Remote Similarity	NPD6013	Approved
0.6579	Remote Similarity	NPD6372	Approved
0.6579	Remote Similarity	NPD6012	Approved
0.6579	Remote Similarity	NPD6014	Approved
0.6579	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD6411	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6549	Remote Similarity	NPD5701	Approved
0.6532	Remote Similarity	NPD8293	Discontinued
0.6522	Remote Similarity	NPD6883	Approved
0.6522	Remote Similarity	NPD7290	Approved
0.6522	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD6399	Phase 3
0.6496	Remote Similarity	NPD4632	Approved
0.6491	Remote Similarity	NPD6686	Approved
0.6491	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6466	Remote Similarity	NPD6847	Approved
0.6466	Remote Similarity	NPD6869	Approved
0.6466	Remote Similarity	NPD6617	Approved
0.6466	Remote Similarity	NPD8130	Phase 1
0.6465	Remote Similarity	NPD4819	Approved
0.6465	Remote Similarity	NPD4820	Approved
0.6465	Remote Similarity	NPD4822	Approved
0.6465	Remote Similarity	NPD4821	Approved
0.6452	Remote Similarity	NPD7507	Approved
0.6436	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4238	Approved
0.6429	Remote Similarity	NPD4802	Phase 2
0.6429	Remote Similarity	NPD4271	Approved
0.6422	Remote Similarity	NPD6083	Phase 2
0.6422	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD7637	Suspended
0.641	Remote Similarity	NPD6882	Approved
0.641	Remote Similarity	NPD8297	Approved
0.6404	Remote Similarity	NPD6412	Phase 2
0.6389	Remote Similarity	NPD5695	Phase 3
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4634	Approved
0.6372	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD5209	Approved
0.6333	Remote Similarity	NPD6009	Approved
0.6321	Remote Similarity	NPD7838	Discovery
0.6311	Remote Similarity	NPD1694	Approved
0.6306	Remote Similarity	NPD5286	Approved
0.6306	Remote Similarity	NPD5285	Approved
0.6306	Remote Similarity	NPD4696	Approved
0.6286	Remote Similarity	NPD6903	Approved
0.6275	Remote Similarity	NPD5331	Approved
0.6275	Remote Similarity	NPD5332	Approved
0.6275	Remote Similarity	NPD4788	Approved
0.6273	Remote Similarity	NPD4755	Approved
0.6262	Remote Similarity	NPD8035	Phase 2
0.6262	Remote Similarity	NPD8034	Phase 2
0.626	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8267	Approved
0.626	Remote Similarity	NPD8269	Approved
0.626	Remote Similarity	NPD8268	Approved
0.626	Remote Similarity	NPD8266	Approved
0.626	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD1700	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD4790	Discontinued
0.6228	Remote Similarity	NPD5141	Approved
0.6218	Remote Similarity	NPD8133	Approved
0.6214	Remote Similarity	NPD3666	Approved
0.6214	Remote Similarity	NPD3665	Phase 1
0.6214	Remote Similarity	NPD3133	Approved
0.6195	Remote Similarity	NPD7632	Discontinued
0.6195	Remote Similarity	NPD5226	Approved
0.6195	Remote Similarity	NPD5225	Approved
0.6195	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD4633	Approved
0.6186	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7839	Suspended
0.6176	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4700	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD6845	Suspended
0.614	Remote Similarity	NPD5175	Approved
0.614	Remote Similarity	NPD5174	Approved
0.6132	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8516	Approved
0.6129	Remote Similarity	NPD8517	Approved
0.6129	Remote Similarity	NPD8515	Approved
0.6129	Remote Similarity	NPD8513	Phase 3
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD5284	Approved
0.6106	Remote Similarity	NPD5223	Approved
0.6098	Remote Similarity	NPD7101	Approved
0.6098	Remote Similarity	NPD7100	Approved
0.6094	Remote Similarity	NPD6033	Approved
0.6091	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5210	Approved
0.6091	Remote Similarity	NPD4629	Approved
0.6077	Remote Similarity	NPD7260	Phase 2
0.6075	Remote Similarity	NPD4753	Phase 2
0.6066	Remote Similarity	NPD6317	Approved
0.6063	Remote Similarity	NPD6336	Discontinued
0.605	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD3667	Approved
0.6017	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6313	Approved
0.6016	Remote Similarity	NPD6314	Approved
0.6016	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6921	Approved
0.6	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD3198	Approved
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6079	Approved
0.5943	Remote Similarity	NPD3618	Phase 1
0.5943	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4729	Approved
0.5932	Remote Similarity	NPD4730	Approved
0.5932	Remote Similarity	NPD5128	Approved
0.5929	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5328	Approved
0.5926	Remote Similarity	NPD6334	Approved
0.5926	Remote Similarity	NPD5370	Suspended
0.5926	Remote Similarity	NPD6333	Approved
0.5909	Remote Similarity	NPD4202	Approved
0.5906	Remote Similarity	NPD8328	Phase 3
0.5905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4786	Approved
0.5897	Remote Similarity	NPD4767	Approved
0.5897	Remote Similarity	NPD4768	Approved
0.5893	Remote Similarity	NPD4697	Phase 3
0.5893	Remote Similarity	NPD5221	Approved
0.5893	Remote Similarity	NPD5222	Approved
0.5893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD8074	Phase 3

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