NPASS Compound

Structure

NPC293001 OpenBabel07101718242D 22 24 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 -6.2387 -0.0299 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 -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 -2.1195 -1.4985 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 -5.7517 0.8435 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 -0.9960 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2389 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8789 -1.5775 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 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 -6.2646 1.7019 0.0000 O 0 0 0 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 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 9 2 0 0 0 0 3 10 1 0 0 0 0 5 8 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 1 1 6 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 7 1 1 0 0 0 11 12 1 0 0 0 0 12 5 1 1 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 6 0 0 0 14 17 1 6 0 0 0 14 19 1 0 0 0 0 15 17 1 1 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	312.961
LogP:	1.972
LogD:	2.218
LogS:	-2.973
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.709
Fsp3:	0.765
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:	-4.878
MDCK Permeability:	6.427492189686745e-05
Pgp-inhibitor:	0.092
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	71.43995666503906%
Volume Distribution (VD):	0.95
Pgp-substrate:	37.692020416259766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.352
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	5.626
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.488
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.317
Skin Sensitization:	0.884
Carcinogencity:	0.435
Eye Corrosion:	0.224
Eye Irritation:	0.647
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC293001

Natural Product ID:	NPC293001
*Common Name:**	6-Deoxychamissonolide
IUPAC Name:	[(3aR,5R,5aS,6S,8R,8aS,9aR)-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate
Synonyms:	6-Deoxychamissonolide
Standard InCHIKey:	JRTIKBMBXBPGNG-YIECKHAFSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-8-5-12-11(9(2)16(20)22-12)7-17(4)14(19)6-13(15(8)17)21-10(3)18/h8,11-15,19H,2,5-7H2,1,3-4H3/t8-,11-,12-,13+,14-,15-,17-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1[C@H](C)C[C@@H]1[C@H](C2)C(=C)C(=O)O1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL372877
PubChem CID:	12443012
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
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[16644542]
NPO5484	Arnica angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO5484	Arnica angustifolia	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	5
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	2
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	200.0	uM	PMID[456025]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	102000.0	nM	PMID[456026]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10600.0	nM	PMID[456026]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[456027]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[456027]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[456027]

☑ 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 NPC293001 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	250
0.1-0.2	1790
0.2-0.3	6417
0.3-0.4	15254
0.4-0.5	8203
0.5-0.6	7313
0.6-0.7	2887
0.7-0.8	432
0.8-0.85	64
0.85-0.9	45
0.9-0.95	24
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC171360
1.0	High Similarity	NPC57304
1.0	High Similarity	NPC29821
1.0	High Similarity	NPC35959
1.0	High Similarity	NPC133888
1.0	High Similarity	NPC63193
0.9882	High Similarity	NPC297474
0.9882	High Similarity	NPC35809
0.9882	High Similarity	NPC54065
0.9765	High Similarity	NPC155935
0.9551	High Similarity	NPC18019
0.9551	High Similarity	NPC24956
0.9529	High Similarity	NPC24728
0.9425	High Similarity	NPC216284
0.9419	High Similarity	NPC217983
0.9419	High Similarity	NPC471149
0.9419	High Similarity	NPC207114
0.9412	High Similarity	NPC56593
0.9333	High Similarity	NPC91771
0.9333	High Similarity	NPC142529
0.931	High Similarity	NPC283409
0.931	High Similarity	NPC215556
0.9222	High Similarity	NPC472873
0.9205	High Similarity	NPC19087
0.9195	High Similarity	NPC79549
0.9186	High Similarity	NPC187661
0.9101	High Similarity	NPC184063
0.9101	High Similarity	NPC155215
0.9091	High Similarity	NPC38392
0.9022	High Similarity	NPC471150
0.9022	High Similarity	NPC311904
0.9011	High Similarity	NPC476053
0.9011	High Similarity	NPC213698
0.9	High Similarity	NPC473234
0.9	High Similarity	NPC200237
0.9	High Similarity	NPC60386
0.9	High Similarity	NPC473263
0.9	High Similarity	NPC258216
0.9	High Similarity	NPC473273
0.9	High Similarity	NPC308656
0.8953	High Similarity	NPC224386
0.8953	High Similarity	NPC194859
0.8941	High Similarity	NPC246076
0.8936	High Similarity	NPC171759
0.8901	High Similarity	NPC127019
0.8901	High Similarity	NPC473331
0.8889	High Similarity	NPC286341
0.8889	High Similarity	NPC191339
0.8889	High Similarity	NPC475925
0.8876	High Similarity	NPC472872
0.8851	High Similarity	NPC284534
0.8851	High Similarity	NPC300082
0.8851	High Similarity	NPC204105
0.8837	High Similarity	NPC128246
0.8837	High Similarity	NPC111409
0.8817	High Similarity	NPC161493
0.8804	High Similarity	NPC170120
0.8804	High Similarity	NPC163228
0.8791	High Similarity	NPC153590
0.875	High Similarity	NPC304558
0.871	High Similarity	NPC213078
0.8667	High Similarity	NPC168679
0.8667	High Similarity	NPC12872
0.8652	High Similarity	NPC118601
0.8652	High Similarity	NPC201658
0.8632	High Similarity	NPC186861
0.8632	High Similarity	NPC471381
0.8621	High Similarity	NPC245665
0.8617	High Similarity	NPC108475
0.8617	High Similarity	NPC170143
0.8617	High Similarity	NPC213947
0.8617	High Similarity	NPC474313
0.8605	High Similarity	NPC126248
0.8602	High Similarity	NPC52044
0.8602	High Similarity	NPC67584
0.8556	High Similarity	NPC178875
0.8539	High Similarity	NPC236692
0.8539	High Similarity	NPC309757
0.8539	High Similarity	NPC64153
0.8526	High Similarity	NPC45125
0.8511	High Similarity	NPC126156
0.8495	Intermediate Similarity	NPC198853
0.8478	Intermediate Similarity	NPC133698
0.8478	Intermediate Similarity	NPC131209
0.8421	Intermediate Similarity	NPC181151
0.8409	Intermediate Similarity	NPC54468
0.8387	Intermediate Similarity	NPC472874
0.8384	Intermediate Similarity	NPC54737
0.8351	Intermediate Similarity	NPC150923
0.8333	Intermediate Similarity	NPC67493
0.8333	Intermediate Similarity	NPC49833
0.8333	Intermediate Similarity	NPC249171
0.8333	Intermediate Similarity	NPC470242
0.8333	Intermediate Similarity	NPC221615
0.8333	Intermediate Similarity	NPC238593
0.8298	Intermediate Similarity	NPC323008
0.8298	Intermediate Similarity	NPC470013
0.8298	Intermediate Similarity	NPC262133
0.8298	Intermediate Similarity	NPC470010
0.8298	Intermediate Similarity	NPC477131
0.8276	Intermediate Similarity	NPC156658
0.8276	Intermediate Similarity	NPC258965
0.8242	Intermediate Similarity	NPC270270
0.8229	Intermediate Similarity	NPC236580
0.8229	Intermediate Similarity	NPC304445
0.8222	Intermediate Similarity	NPC235792
0.8211	Intermediate Similarity	NPC304886
0.82	Intermediate Similarity	NPC44004
0.8191	Intermediate Similarity	NPC475788
0.8182	Intermediate Similarity	NPC473148
0.8182	Intermediate Similarity	NPC47635
0.8182	Intermediate Similarity	NPC221421
0.8172	Intermediate Similarity	NPC301969
0.8172	Intermediate Similarity	NPC37607
0.8152	Intermediate Similarity	NPC224652
0.8152	Intermediate Similarity	NPC91248
0.8137	Intermediate Similarity	NPC139838
0.8137	Intermediate Similarity	NPC59489
0.8132	Intermediate Similarity	NPC162071
0.8111	Intermediate Similarity	NPC156485
0.8095	Intermediate Similarity	NPC471382
0.8081	Intermediate Similarity	NPC80144
0.8068	Intermediate Similarity	NPC73052
0.8068	Intermediate Similarity	NPC293418
0.8068	Intermediate Similarity	NPC51507
0.8068	Intermediate Similarity	NPC290508
0.8068	Intermediate Similarity	NPC6823
0.8061	Intermediate Similarity	NPC70865
0.8043	Intermediate Similarity	NPC190753
0.8043	Intermediate Similarity	NPC186148
0.8041	Intermediate Similarity	NPC477949
0.8039	Intermediate Similarity	NPC68248
0.8021	Intermediate Similarity	NPC167893
0.8021	Intermediate Similarity	NPC37408
0.8021	Intermediate Similarity	NPC259042
0.8021	Intermediate Similarity	NPC157686
0.8	Intermediate Similarity	NPC143979
0.8	Intermediate Similarity	NPC320537
0.8	Intermediate Similarity	NPC135776
0.798	Intermediate Similarity	NPC67296
0.798	Intermediate Similarity	NPC477950
0.7979	Intermediate Similarity	NPC474323
0.7979	Intermediate Similarity	NPC206614
0.7957	Intermediate Similarity	NPC177629
0.7957	Intermediate Similarity	NPC58219
0.7938	Intermediate Similarity	NPC476009
0.7938	Intermediate Similarity	NPC284518
0.7938	Intermediate Similarity	NPC474297
0.7925	Intermediate Similarity	NPC471380
0.7921	Intermediate Similarity	NPC203659
0.7917	Intermediate Similarity	NPC148000
0.7917	Intermediate Similarity	NPC225474
0.7917	Intermediate Similarity	NPC469596
0.79	Intermediate Similarity	NPC86077
0.79	Intermediate Similarity	NPC225353
0.7872	Intermediate Similarity	NPC92974
0.7872	Intermediate Similarity	NPC4986
0.787	Intermediate Similarity	NPC161060
0.7857	Intermediate Similarity	NPC169205
0.7857	Intermediate Similarity	NPC263674
0.7857	Intermediate Similarity	NPC261372
0.7857	Intermediate Similarity	NPC473963
0.7857	Intermediate Similarity	NPC58267
0.7843	Intermediate Similarity	NPC243998
0.7835	Intermediate Similarity	NPC224689
0.7835	Intermediate Similarity	NPC475900
0.7835	Intermediate Similarity	NPC469873
0.7835	Intermediate Similarity	NPC48803
0.7835	Intermediate Similarity	NPC193645
0.7835	Intermediate Similarity	NPC90121
0.7835	Intermediate Similarity	NPC275960
0.783	Intermediate Similarity	NPC273242
0.7822	Intermediate Similarity	NPC474775
0.7822	Intermediate Similarity	NPC124881
0.7822	Intermediate Similarity	NPC110989
0.7789	Intermediate Similarity	NPC469368
0.7788	Intermediate Similarity	NPC115352
0.7778	Intermediate Similarity	NPC36754
0.7778	Intermediate Similarity	NPC141191
0.7767	Intermediate Similarity	NPC26617
0.7766	Intermediate Similarity	NPC202672
0.7757	Intermediate Similarity	NPC121816
0.7757	Intermediate Similarity	NPC123117
0.7755	Intermediate Similarity	NPC93245
0.7755	Intermediate Similarity	NPC185553
0.7755	Intermediate Similarity	NPC473964
0.7753	Intermediate Similarity	NPC19841
0.7742	Intermediate Similarity	NPC475019
0.7742	Intermediate Similarity	NPC474949
0.7732	Intermediate Similarity	NPC24861
0.7727	Intermediate Similarity	NPC208223
0.7714	Intermediate Similarity	NPC471884
0.7708	Intermediate Similarity	NPC12172
0.7708	Intermediate Similarity	NPC208886
0.7708	Intermediate Similarity	NPC184463
0.7708	Intermediate Similarity	NPC221282
0.77	Intermediate Similarity	NPC47024
0.7692	Intermediate Similarity	NPC89555
0.7692	Intermediate Similarity	NPC255082
0.7692	Intermediate Similarity	NPC212340

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 NPC293001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	2514
0.2-0.3	3897
0.3-0.4	1688
0.4-0.5	405
0.5-0.6	279
0.6-0.7	48
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
0.7872	Intermediate Similarity	NPD1695	Approved
0.7835	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4249	Approved
0.7547	Intermediate Similarity	NPD6371	Approved
0.7474	Intermediate Similarity	NPD4250	Approved
0.7474	Intermediate Similarity	NPD4251	Approved
0.7423	Intermediate Similarity	NPD5785	Approved
0.7248	Intermediate Similarity	NPD6053	Discontinued
0.7128	Intermediate Similarity	NPD6435	Approved
0.7097	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD7638	Approved
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6915	Remote Similarity	NPD5368	Approved
0.6915	Remote Similarity	NPD4821	Approved
0.6907	Remote Similarity	NPD5363	Approved
0.69	Remote Similarity	NPD6698	Approved
0.69	Remote Similarity	NPD46	Approved
0.6882	Remote Similarity	NPD4268	Approved
0.6882	Remote Similarity	NPD4271	Approved
0.6875	Remote Similarity	NPD7154	Phase 3
0.6863	Remote Similarity	NPD5282	Discontinued
0.6857	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD5369	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4269	Approved
0.6735	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6686	Approved
0.6697	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6604	Remote Similarity	NPD4225	Approved
0.6602	Remote Similarity	NPD6399	Phase 3
0.6569	Remote Similarity	NPD7838	Discovery
0.6562	Remote Similarity	NPD4252	Approved
0.6531	Remote Similarity	NPD5331	Approved
0.6531	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6083	Phase 2
0.6509	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD8034	Phase 2
0.6505	Remote Similarity	NPD8035	Phase 2
0.6495	Remote Similarity	NPD4790	Discontinued
0.6486	Remote Similarity	NPD6412	Phase 2
0.6486	Remote Similarity	NPD5697	Approved
0.6476	Remote Similarity	NPD5695	Phase 3
0.6449	Remote Similarity	NPD5696	Approved
0.6435	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6422	Remote Similarity	NPD7632	Discontinued
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD1694	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6393	Remote Similarity	NPD7507	Approved
0.6373	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD4788	Approved
0.6346	Remote Similarity	NPD7983	Approved
0.6346	Remote Similarity	NPD7637	Suspended
0.6339	Remote Similarity	NPD5701	Approved
0.6337	Remote Similarity	NPD6684	Approved
0.6337	Remote Similarity	NPD5330	Approved
0.6337	Remote Similarity	NPD7521	Approved
0.6337	Remote Similarity	NPD7334	Approved
0.6337	Remote Similarity	NPD7146	Approved
0.6337	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD6883	Approved
0.6311	Remote Similarity	NPD7492	Approved
0.63	Remote Similarity	NPD3665	Phase 1
0.63	Remote Similarity	NPD3133	Approved
0.63	Remote Similarity	NPD3666	Approved
0.6293	Remote Similarity	NPD4632	Approved
0.6286	Remote Similarity	NPD5779	Approved
0.6286	Remote Similarity	NPD5778	Approved
0.6283	Remote Similarity	NPD6011	Approved
0.6279	Remote Similarity	NPD3198	Approved
0.6271	Remote Similarity	NPD7115	Discovery
0.6261	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6617	Approved
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6319	Approved
0.624	Remote Similarity	NPD7319	Approved
0.6238	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7078	Approved
0.6207	Remote Similarity	NPD6882	Approved
0.6207	Remote Similarity	NPD8297	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.6198	Remote Similarity	NPD8033	Approved
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD5281	Approved
0.619	Remote Similarity	NPD5284	Approved
0.6186	Remote Similarity	NPD4238	Approved
0.6186	Remote Similarity	NPD4802	Phase 2
0.6174	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5210	Approved
0.6168	Remote Similarity	NPD4629	Approved
0.6168	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.6148	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6147	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6009	Approved
0.6126	Remote Similarity	NPD5211	Phase 2
0.6116	Remote Similarity	NPD6059	Approved
0.61	Remote Similarity	NPD5209	Approved
0.61	Remote Similarity	NPD3667	Approved
0.6095	Remote Similarity	NPD5207	Approved
0.6091	Remote Similarity	NPD4696	Approved
0.6091	Remote Similarity	NPD5285	Approved
0.6091	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD7327	Approved
0.6083	Remote Similarity	NPD7328	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.6066	Remote Similarity	NPD5983	Phase 2
0.6066	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD6685	Approved
0.605	Remote Similarity	NPD6274	Approved
0.604	Remote Similarity	NPD6695	Phase 3
0.6036	Remote Similarity	NPD5344	Discontinued
0.6036	Remote Similarity	NPD1700	Approved
0.6033	Remote Similarity	NPD7516	Approved
0.6019	Remote Similarity	NPD3618	Phase 1
0.6018	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5984	Remote Similarity	NPD8377	Approved
0.5984	Remote Similarity	NPD8294	Approved
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4633	Approved
0.5982	Remote Similarity	NPD5224	Approved
0.5982	Remote Similarity	NPD5225	Approved
0.5982	Remote Similarity	NPD5226	Approved
0.5981	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD4786	Approved
0.5969	Remote Similarity	NPD6845	Suspended
0.5968	Remote Similarity	NPD7604	Phase 2
0.5946	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8380	Approved
0.5935	Remote Similarity	NPD8378	Approved
0.5935	Remote Similarity	NPD8296	Approved
0.5935	Remote Similarity	NPD8335	Approved
0.5935	Remote Similarity	NPD7503	Approved
0.5935	Remote Similarity	NPD8379	Approved
0.5929	Remote Similarity	NPD5174	Approved
0.5929	Remote Similarity	NPD5175	Approved
0.5926	Remote Similarity	NPD6001	Approved
0.5913	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7902	Approved
0.5905	Remote Similarity	NPD6672	Approved
0.5905	Remote Similarity	NPD5737	Approved
0.5902	Remote Similarity	NPD7100	Approved
0.5902	Remote Similarity	NPD7101	Approved
0.5897	Remote Similarity	NPD4634	Approved
0.5893	Remote Similarity	NPD5223	Approved
0.5891	Remote Similarity	NPD7260	Phase 2
0.5876	Remote Similarity	NPD3702	Approved
0.5873	Remote Similarity	NPD6336	Discontinued
0.5868	Remote Similarity	NPD6317	Approved
0.5865	Remote Similarity	NPD5279	Phase 3
0.5859	Remote Similarity	NPD6118	Approved
0.5859	Remote Similarity	NPD6114	Approved
0.5859	Remote Similarity	NPD6115	Approved
0.5859	Remote Similarity	NPD6697	Approved
0.5849	Remote Similarity	NPD6080	Approved
0.5849	Remote Similarity	NPD6673	Approved
0.5849	Remote Similarity	NPD6051	Approved
0.5849	Remote Similarity	NPD6904	Approved
0.584	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