NPASS Compound

Structure

CID191339 OpenBabel06191715572D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.9403 1.5342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2604 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3731 -4.3318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9572 -1.1739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1069 1.6677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5595 0.6666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4604 -0.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5224 0.6666 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3467 -1.5190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3731 -3.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9591 -0.0863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0819 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7352 -1.5190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1734 -1.0251 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1228 -0.0863 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0410 -1.4430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3785 -0.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9086 -1.0251 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4609 -2.8874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8215 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3173 -1.0998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5758 0.8267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0410 -2.4059 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 9 2 0 0 0 0 3 10 1 0 0 0 0 5 22 1 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 1 1 6 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 19 2 0 0 0 0 10 23 1 0 0 0 0 11 6 1 6 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 6 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 15 18 1 1 0 0 0 16 18 1 6 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.16
Volume:	336.41
LogP:	1.049
LogD:	1.735
LogS:	-3.16
# Rotatable Bonds:	3
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.673
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:	-4.752
MDCK Permeability:	4.6783436118857935e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.185
20% Bioavailability (F20%):	0.729
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.93
Plasma Protein Binding (PPB):	29.0146484375%
Volume Distribution (VD):	0.453
Pgp-substrate:	58.97694778442383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.677
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	8.919
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.715
Carcinogencity:	0.638
Eye Corrosion:	0.929
Eye Irritation:	0.773
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: NPC191339

Natural Product ID:	NPC191339
*Common Name:**	(1S,2S,5R,6S,7R,8S,10R)-6-Acetoxy-2-Methoxy-4-Oxopseudoguai-11(13)-En-12,8-Olide
IUPAC Name:	[(3aS,5R,5aS,6S,8aR,9S,9aR)-6-methoxy-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-9-yl] acetate
Synonyms:
Standard InCHIKey:	IVGBVLQEASLHGO-PIALLGAOSA-N
Standard InCHI:	InChI=1S/C18H24O6/c1-8-6-11-14(9(2)17(21)24-11)16(23-10(3)19)18(4)13(20)7-12(22-5)15(8)18/h8,11-12,14-16H,2,6-7H2,1,3-5H3/t8-,11+,12+,14-,15-,16+,18-/m1/s1
SMILES:	C[C@@H]1C[C@H]2[C@@H](C(=C)C(=O)O2)[C@@H]([C@]2(C)C(=O)C[C@@H]([C@@H]12)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911134
PubChem CID:	54669755
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	=	1500.0	nM	PMID[549020]

☑ 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 NPC191339 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	290
0.1-0.2	2275
0.2-0.3	7595
0.3-0.4	14376
0.4-0.5	9199
0.5-0.6	6200
0.6-0.7	2300
0.7-0.8	354
0.8-0.85	44
0.85-0.9	44
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC286341
0.9551	High Similarity	NPC142529
0.9551	High Similarity	NPC91771
0.9412	High Similarity	NPC238593
0.9302	High Similarity	NPC24728
0.9213	High Similarity	NPC473263
0.9213	High Similarity	NPC473234
0.9213	High Similarity	NPC200237
0.9213	High Similarity	NPC60386
0.9213	High Similarity	NPC473273
0.9213	High Similarity	NPC153590
0.9213	High Similarity	NPC308656
0.9195	High Similarity	NPC471149
0.9186	High Similarity	NPC304558
0.914	High Similarity	NPC171759
0.9091	High Similarity	NPC283409
0.9059	High Similarity	NPC54468
0.8989	High Similarity	NPC54065
0.8989	High Similarity	NPC297474
0.8941	High Similarity	NPC246076
0.8901	High Similarity	NPC473331
0.8889	High Similarity	NPC133888
0.8889	High Similarity	NPC57304
0.8889	High Similarity	NPC293001
0.8889	High Similarity	NPC171360
0.8889	High Similarity	NPC35959
0.8889	High Similarity	NPC63193
0.8889	High Similarity	NPC29821
0.8876	High Similarity	NPC168679
0.8876	High Similarity	NPC12872
0.8876	High Similarity	NPC155935
0.8817	High Similarity	NPC213947
0.8817	High Similarity	NPC108475
0.8817	High Similarity	NPC170143
0.8817	High Similarity	NPC311904
0.8804	High Similarity	NPC163228
0.8778	High Similarity	NPC19087
0.8778	High Similarity	NPC35809
0.871	High Similarity	NPC126156
0.8706	High Similarity	NPC73052
0.8706	High Similarity	NPC290508
0.8706	High Similarity	NPC6823
0.8706	High Similarity	NPC293418
0.8681	High Similarity	NPC184063
0.8667	High Similarity	NPC38392
0.8667	High Similarity	NPC472872
0.8652	High Similarity	NPC270270
0.8652	High Similarity	NPC118601
0.8652	High Similarity	NPC201658
0.8602	High Similarity	NPC476053
0.8556	High Similarity	NPC79549
0.8556	High Similarity	NPC178875
0.8556	High Similarity	NPC207114
0.8556	High Similarity	NPC217983
0.8539	High Similarity	NPC56593
0.8539	High Similarity	NPC64153
0.8511	High Similarity	NPC18019
0.8511	High Similarity	NPC24956
0.8478	Intermediate Similarity	NPC74103
0.8478	Intermediate Similarity	NPC123177
0.8478	Intermediate Similarity	NPC150978
0.8478	Intermediate Similarity	NPC70595
0.8462	Intermediate Similarity	NPC215556
0.8421	Intermediate Similarity	NPC471150
0.8391	Intermediate Similarity	NPC47635
0.837	Intermediate Similarity	NPC253144
0.837	Intermediate Similarity	NPC216284
0.8353	Intermediate Similarity	NPC208223
0.8333	Intermediate Similarity	NPC187661
0.8333	Intermediate Similarity	NPC236692
0.8333	Intermediate Similarity	NPC309757
0.828	Intermediate Similarity	NPC284185
0.828	Intermediate Similarity	NPC155215
0.828	Intermediate Similarity	NPC221282
0.8247	Intermediate Similarity	NPC186861
0.8229	Intermediate Similarity	NPC474313
0.8222	Intermediate Similarity	NPC235792
0.8222	Intermediate Similarity	NPC284534
0.8222	Intermediate Similarity	NPC204105
0.8222	Intermediate Similarity	NPC300082
0.8211	Intermediate Similarity	NPC475900
0.8211	Intermediate Similarity	NPC472873
0.8191	Intermediate Similarity	NPC258216
0.8191	Intermediate Similarity	NPC472874
0.8152	Intermediate Similarity	NPC224652
0.8125	Intermediate Similarity	NPC476009
0.8111	Intermediate Similarity	NPC224386
0.8111	Intermediate Similarity	NPC194859
0.8105	Intermediate Similarity	NPC127019
0.81	Intermediate Similarity	NPC203659
0.8085	Intermediate Similarity	NPC475925
0.8081	Intermediate Similarity	NPC225353
0.8061	Intermediate Similarity	NPC471381
0.8041	Intermediate Similarity	NPC169205
0.8021	Intermediate Similarity	NPC193645
0.8021	Intermediate Similarity	NPC167893
0.8021	Intermediate Similarity	NPC213698
0.8021	Intermediate Similarity	NPC275960
0.8021	Intermediate Similarity	NPC48803
0.8021	Intermediate Similarity	NPC90121
0.8021	Intermediate Similarity	NPC67584
0.802	Intermediate Similarity	NPC291643
0.8	Intermediate Similarity	NPC215294
0.8	Intermediate Similarity	NPC128246
0.8	Intermediate Similarity	NPC320537
0.8	Intermediate Similarity	NPC111409
0.8	Intermediate Similarity	NPC143979
0.8	Intermediate Similarity	NPC135776
0.8	Intermediate Similarity	NPC110989
0.8	Intermediate Similarity	NPC245665
0.798	Intermediate Similarity	NPC477950
0.798	Intermediate Similarity	NPC471767
0.7959	Intermediate Similarity	NPC141191
0.7959	Intermediate Similarity	NPC54843
0.7959	Intermediate Similarity	NPC470188
0.7938	Intermediate Similarity	NPC185553
0.7938	Intermediate Similarity	NPC213078
0.7935	Intermediate Similarity	NPC104961
0.7935	Intermediate Similarity	NPC70555
0.7935	Intermediate Similarity	NPC70422
0.7935	Intermediate Similarity	NPC470242
0.7917	Intermediate Similarity	NPC198853
0.79	Intermediate Similarity	NPC105725
0.79	Intermediate Similarity	NPC250594
0.7895	Intermediate Similarity	NPC290651
0.7895	Intermediate Similarity	NPC133698
0.7872	Intermediate Similarity	NPC4986
0.7865	Intermediate Similarity	NPC51507
0.7857	Intermediate Similarity	NPC161493
0.7857	Intermediate Similarity	NPC477949
0.7849	Intermediate Similarity	NPC190753
0.7843	Intermediate Similarity	NPC54737
0.7843	Intermediate Similarity	NPC44004
0.7835	Intermediate Similarity	NPC224689
0.7835	Intermediate Similarity	NPC170120
0.7835	Intermediate Similarity	NPC52044
0.7826	Intermediate Similarity	NPC21471
0.7826	Intermediate Similarity	NPC33570
0.7826	Intermediate Similarity	NPC161957
0.7812	Intermediate Similarity	NPC475788
0.7802	Intermediate Similarity	NPC318468
0.7802	Intermediate Similarity	NPC128429
0.7789	Intermediate Similarity	NPC62815
0.7778	Intermediate Similarity	NPC126248
0.7778	Intermediate Similarity	NPC45125
0.7765	Intermediate Similarity	NPC470243
0.7755	Intermediate Similarity	NPC118159
0.7745	Intermediate Similarity	NPC100487
0.7742	Intermediate Similarity	NPC469676
0.7742	Intermediate Similarity	NPC107787
0.7742	Intermediate Similarity	NPC67493
0.7732	Intermediate Similarity	NPC470013
0.7732	Intermediate Similarity	NPC477131
0.7732	Intermediate Similarity	NPC323008
0.7732	Intermediate Similarity	NPC140543
0.7732	Intermediate Similarity	NPC470010
0.7732	Intermediate Similarity	NPC476267
0.7732	Intermediate Similarity	NPC262133
0.7723	Intermediate Similarity	NPC474747
0.7723	Intermediate Similarity	NPC80144
0.7723	Intermediate Similarity	NPC49393
0.7717	Intermediate Similarity	NPC470238
0.7717	Intermediate Similarity	NPC138647
0.7717	Intermediate Similarity	NPC115786
0.7708	Intermediate Similarity	NPC131209
0.7708	Intermediate Similarity	NPC20713
0.7701	Intermediate Similarity	NPC471491
0.77	Intermediate Similarity	NPC280963
0.7684	Intermediate Similarity	NPC32922
0.7677	Intermediate Similarity	NPC181151
0.7667	Intermediate Similarity	NPC69271
0.7667	Intermediate Similarity	NPC258965
0.7667	Intermediate Similarity	NPC474981
0.7667	Intermediate Similarity	NPC223904
0.7667	Intermediate Similarity	NPC74673
0.7667	Intermediate Similarity	NPC156658
0.766	Intermediate Similarity	NPC5130
0.766	Intermediate Similarity	NPC186148
0.7647	Intermediate Similarity	NPC475871
0.7647	Intermediate Similarity	NPC475945
0.7647	Intermediate Similarity	NPC221421
0.7642	Intermediate Similarity	NPC475495
0.7634	Intermediate Similarity	NPC78089
0.7624	Intermediate Similarity	NPC474053
0.7624	Intermediate Similarity	NPC474742
0.7624	Intermediate Similarity	NPC150923
0.7624	Intermediate Similarity	NPC304624
0.7624	Intermediate Similarity	NPC475099
0.7624	Intermediate Similarity	NPC67296
0.7619	Intermediate Similarity	NPC139838
0.7619	Intermediate Similarity	NPC59489
0.7609	Intermediate Similarity	NPC272814
0.7609	Intermediate Similarity	NPC474472
0.7609	Intermediate Similarity	NPC39588
0.7609	Intermediate Similarity	NPC257358
0.7604	Intermediate Similarity	NPC106510
0.7604	Intermediate Similarity	NPC37607
0.7604	Intermediate Similarity	NPC475776
0.7604	Intermediate Similarity	NPC301969
0.7604	Intermediate Similarity	NPC246173

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 NPC191339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	2934
0.2-0.3	3818
0.3-0.4	1390
0.4-0.5	392
0.5-0.6	222
0.6-0.7	43
0.7-0.8	5
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
0.8021	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1695	Approved
0.7596	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6371	Approved
0.7245	Intermediate Similarity	NPD5785	Approved
0.717	Intermediate Similarity	NPD6008	Approved
0.7083	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5282	Discontinued
0.6837	Remote Similarity	NPD5786	Approved
0.6786	Remote Similarity	NPD6053	Discontinued
0.6771	Remote Similarity	NPD6435	Approved
0.6735	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.66	Remote Similarity	NPD4251	Approved
0.66	Remote Similarity	NPD4250	Approved
0.6598	Remote Similarity	NPD4269	Approved
0.6598	Remote Similarity	NPD5209	Approved
0.6598	Remote Similarity	NPD4270	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD5368	Approved
0.6535	Remote Similarity	NPD6903	Approved
0.65	Remote Similarity	NPD7146	Approved
0.65	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD7334	Approved
0.65	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD5330	Approved
0.65	Remote Similarity	NPD6684	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6616	Approved
0.6392	Remote Similarity	NPD4252	Approved
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6319	Approved
0.6373	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5362	Discontinued
0.6346	Remote Similarity	NPD5693	Phase 1
0.6346	Remote Similarity	NPD7983	Approved
0.6341	Remote Similarity	NPD7078	Approved
0.6339	Remote Similarity	NPD5697	Approved
0.6333	Remote Similarity	NPD6015	Approved
0.6333	Remote Similarity	NPD6016	Approved
0.6321	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD7638	Approved
0.629	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD5778	Approved
0.6286	Remote Similarity	NPD6399	Phase 3
0.6286	Remote Similarity	NPD5779	Approved
0.6283	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD7320	Approved
0.6283	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6899	Approved
0.6281	Remote Similarity	NPD6370	Approved
0.6281	Remote Similarity	NPD5988	Approved
0.6261	Remote Similarity	NPD6650	Approved
0.6261	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD46	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD5207	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD6698	Approved
0.624	Remote Similarity	NPD7319	Approved
0.6239	Remote Similarity	NPD7640	Approved
0.6239	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD6372	Approved
0.6228	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6014	Approved
0.6228	Remote Similarity	NPD6012	Approved
0.6228	Remote Similarity	NPD6373	Approved
0.6224	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8293	Discontinued
0.6195	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD6411	Approved
0.6186	Remote Similarity	NPD4238	Approved
0.6186	Remote Similarity	NPD4802	Phase 2
0.6174	Remote Similarity	NPD7290	Approved
0.6174	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD4632	Approved
0.6147	Remote Similarity	NPD5696	Approved
0.614	Remote Similarity	NPD6011	Approved
0.614	Remote Similarity	NPD6686	Approved
0.6134	Remote Similarity	NPD7115	Discovery
0.6129	Remote Similarity	NPD7507	Approved
0.6121	Remote Similarity	NPD6847	Approved
0.6121	Remote Similarity	NPD6617	Approved
0.6121	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD229	Approved
0.6075	Remote Similarity	NPD6001	Approved
0.6068	Remote Similarity	NPD8297	Approved
0.6068	Remote Similarity	NPD6882	Approved
0.6061	Remote Similarity	NPD4819	Approved
0.6061	Remote Similarity	NPD4822	Approved
0.6061	Remote Similarity	NPD4821	Approved
0.6061	Remote Similarity	NPD4820	Approved
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD5737	Approved
0.6055	Remote Similarity	NPD6083	Phase 2
0.6055	Remote Similarity	NPD6084	Phase 2
0.6053	Remote Similarity	NPD6412	Phase 2
0.604	Remote Similarity	NPD7154	Phase 3
0.6038	Remote Similarity	NPD7637	Suspended
0.6038	Remote Similarity	NPD8034	Phase 2
0.6038	Remote Similarity	NPD8035	Phase 2
0.6036	Remote Similarity	NPD1700	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.602	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4271	Approved
0.602	Remote Similarity	NPD4268	Approved
0.6018	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6101	Approved
0.5982	Remote Similarity	NPD5211	Phase 2
0.5969	Remote Similarity	NPD6845	Suspended
0.5946	Remote Similarity	NPD5285	Approved
0.5946	Remote Similarity	NPD5286	Approved
0.5946	Remote Similarity	NPD4696	Approved
0.5943	Remote Similarity	NPD5692	Phase 3
0.5943	Remote Similarity	NPD7838	Discovery
0.5935	Remote Similarity	NPD5983	Phase 2
0.5935	Remote Similarity	NPD8268	Approved
0.5935	Remote Similarity	NPD8266	Approved
0.5935	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8269	Approved
0.5935	Remote Similarity	NPD8267	Approved
0.5917	Remote Similarity	NPD6274	Approved
0.5913	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4755	Approved
0.5905	Remote Similarity	NPD5208	Approved
0.5895	Remote Similarity	NPD5777	Approved
0.5891	Remote Similarity	NPD7260	Phase 2
0.5888	Remote Similarity	NPD5694	Approved
0.5888	Remote Similarity	NPD5284	Approved
0.5888	Remote Similarity	NPD5281	Approved
0.5888	Remote Similarity	NPD6050	Approved
0.5882	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD8133	Approved
0.5882	Remote Similarity	NPD4788	Approved
0.5882	Remote Similarity	NPD5331	Approved
0.5877	Remote Similarity	NPD5141	Approved
0.5865	Remote Similarity	NPD6098	Approved
0.5849	Remote Similarity	NPD6051	Approved
0.5847	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4790	Discontinued
0.5841	Remote Similarity	NPD5226	Approved
0.5841	Remote Similarity	NPD4633	Approved
0.5841	Remote Similarity	NPD5225	Approved
0.5841	Remote Similarity	NPD7632	Discontinued
0.5841	Remote Similarity	NPD5224	Approved
0.584	Remote Similarity	NPD7604	Phase 2
0.5825	Remote Similarity	NPD3665	Phase 1
0.5825	Remote Similarity	NPD3133	Approved
0.5825	Remote Similarity	NPD3666	Approved
0.5818	Remote Similarity	NPD7839	Suspended
0.5806	Remote Similarity	NPD8517	Approved
0.5806	Remote Similarity	NPD8513	Phase 3
0.5806	Remote Similarity	NPD8516	Approved
0.5806	Remote Similarity	NPD8515	Approved
0.5804	Remote Similarity	NPD4700	Approved
0.5789	Remote Similarity	NPD6052	Approved
0.5789	Remote Similarity	NPD5174	Approved
0.5789	Remote Similarity	NPD5175	Approved
0.5781	Remote Similarity	NPD6033	Approved
0.578	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7900	Approved
0.5772	Remote Similarity	NPD7100	Approved
0.5772	Remote Similarity	NPD7101	Approved
0.5763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5223	Approved
0.5748	Remote Similarity	NPD6336	Discontinued
0.5738	Remote Similarity	NPD6317	Approved
0.5727	Remote Similarity	NPD5210	Approved
0.5727	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4753	Phase 2
0.5692	Remote Similarity	NPD5956	Approved
0.5691	Remote Similarity	NPD6313	Approved
0.5691	Remote Similarity	NPD6314	Approved
0.5691	Remote Similarity	NPD6335	Approved
0.568	Remote Similarity	NPD6921	Approved
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD3668	Phase 3
0.566	Remote Similarity	NPD3573	Approved
0.5659	Remote Similarity	NPD8336	Approved
0.5659	Remote Similarity	NPD8337	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