NPASS Compound

Structure

NPC474032 OpenBabel07101719522D 22 23 0 0 1 0 0 0 0 0999 V2000 4.5493 2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0594 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5009 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 1.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2618 -1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 1.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 -0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 1.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2673 -1.3090 0.0000 C 0 0 0 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 -0.2929 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2129 0.4428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0361 -1.8383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2074 0.5473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 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 1 9 1 0 0 0 0 2 10 2 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 8 14 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 7 1 6 0 0 0 13 16 1 0 0 0 0 14 19 1 1 0 0 0 15 16 1 0 0 0 0 15 21 1 1 0 0 0 16 22 1 1 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	316.244
LogP:	1.677
LogD:	2.044
LogS:	-2.775
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	4.922
Fsp3:	0.529
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:	-4.742
MDCK Permeability:	9.260445949621499e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.696
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.648

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	59.686180114746094%
Volume Distribution (VD):	0.803
Pgp-substrate:	48.478904724121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.149
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	7.915
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.863
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.416
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.468
Carcinogencity:	0.869
Eye Corrosion:	0.472
Eye Irritation:	0.193
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC474032

Natural Product ID:	NPC474032
*Common Name:**	[(3As,5Z,7S,11R,11As)-7-Hydroxy-6-Methyl-3,10-Dimethylidene-2-Oxo-4,7,8,9,11,11A-Hexahydro-3Ah-Cyclodeca[B]Furan-11-Yl] Acetate
IUPAC Name:	[(3aS,5Z,7S,11R,11aS)-7-hydroxy-6-methyl-3,10-dimethylidene-2-oxo-4,7,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-11-yl] acetate
Synonyms:
Standard InCHIKey:	IUNWNPFOQLQMNV-VHOZIYFXSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-9-5-7-13-11(3)17(20)22-16(13)15(21-12(4)18)10(2)6-8-14(9)19/h5,13-16,19H,2-3,6-8H2,1,4H3/b9-5-/t13-,14-,15+,16-/m0/s1
SMILES:	CC(=O)O[C@@H]1C(=C)CC[C@H](O)/C(=CC[C@@H]2[C@@H]1OC(=O)C2=C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458729
PubChem CID:	44588118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO8480	Gonospermum fruticosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053514]
NPO22963	Gonospermum gomerae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053514]
NPO22963	Gonospermum gomerae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8480	Gonospermum fruticosum	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	4
Others	5

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	=	19500.0	nM	PMID[522312]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	10000.0	nM	PMID[522312]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	16000.0	nM	PMID[522312]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	56600.0	nM	PMID[522312]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	12.2	%	PMID[522312]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	35.6	%	PMID[522312]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	20.0	%	PMID[522312]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	29.6	%	PMID[522312]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	16.0	%	PMID[522312]

☑ 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 NPC474032 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	191
0.1-0.2	1158
0.2-0.3	4536
0.3-0.4	8983
0.4-0.5	14936
0.5-0.6	7495
0.6-0.7	4051
0.7-0.8	1046
0.8-0.85	207
0.85-0.9	69
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC57405
0.9318	High Similarity	NPC303942
0.931	High Similarity	NPC473321
0.9286	High Similarity	NPC21469
0.9205	High Similarity	NPC475912
0.9205	High Similarity	NPC295204
0.9205	High Similarity	NPC273579
0.9205	High Similarity	NPC288240
0.9205	High Similarity	NPC162205
0.9195	High Similarity	NPC473619
0.9195	High Similarity	NPC476004
0.9195	High Similarity	NPC474761
0.9186	High Similarity	NPC473715
0.9111	High Similarity	NPC473859
0.9101	High Similarity	NPC474035
0.9101	High Similarity	NPC81386
0.9091	High Similarity	NPC30515
0.908	High Similarity	NPC295312
0.9022	High Similarity	NPC288876
0.9	High Similarity	NPC14961
0.9	High Similarity	NPC477922
0.9	High Similarity	NPC270013
0.9	High Similarity	NPC475659
0.9	High Similarity	NPC471142
0.9	High Similarity	NPC36954
0.8989	High Similarity	NPC179746
0.8989	High Similarity	NPC81419
0.8977	High Similarity	NPC51004
0.8966	High Similarity	NPC202672
0.8901	High Similarity	NPC279621
0.8901	High Similarity	NPC477921
0.8901	High Similarity	NPC476315
0.8876	High Similarity	NPC184463
0.8876	High Similarity	NPC208886
0.8876	High Similarity	NPC12172
0.8864	High Similarity	NPC307411
0.8837	High Similarity	NPC255307
0.8778	High Similarity	NPC475838
0.8778	High Similarity	NPC476300
0.8778	High Similarity	NPC228451
0.8778	High Similarity	NPC212486
0.8778	High Similarity	NPC125674
0.8764	High Similarity	NPC475855
0.875	High Similarity	NPC227379
0.875	High Similarity	NPC153805
0.875	High Similarity	NPC474471
0.8736	High Similarity	NPC305475
0.8736	High Similarity	NPC475461
0.8721	High Similarity	NPC141193
0.8721	High Similarity	NPC96259
0.8721	High Similarity	NPC476804
0.8721	High Similarity	NPC114979
0.8721	High Similarity	NPC191476
0.871	High Similarity	NPC473326
0.8681	High Similarity	NPC474247
0.8675	High Similarity	NPC196653
0.8675	High Similarity	NPC471465
0.8652	High Similarity	NPC151770
0.8636	High Similarity	NPC231889
0.8621	High Similarity	NPC38468
0.8621	High Similarity	NPC137033
0.8621	High Similarity	NPC319795
0.8621	High Similarity	NPC50362
0.8605	High Similarity	NPC473390
0.8605	High Similarity	NPC40746
0.8605	High Similarity	NPC131669
0.8605	High Similarity	NPC169575
0.8605	High Similarity	NPC250315
0.8588	High Similarity	NPC24417
0.8556	High Similarity	NPC106510
0.8556	High Similarity	NPC474232
0.8556	High Similarity	NPC179394
0.8556	High Similarity	NPC71533
0.8556	High Similarity	NPC144133
0.8554	High Similarity	NPC7563
0.8554	High Similarity	NPC116177
0.8554	High Similarity	NPC320630
0.8539	High Similarity	NPC476803
0.8523	High Similarity	NPC284902
0.8523	High Similarity	NPC469910
0.8511	High Similarity	NPC474213
0.8511	High Similarity	NPC471144
0.8506	High Similarity	NPC70424
0.8506	High Similarity	NPC158756
0.8506	High Similarity	NPC472957
0.8506	High Similarity	NPC474780
0.8506	High Similarity	NPC243618
0.8506	High Similarity	NPC472958
0.8495	Intermediate Similarity	NPC230800
0.8488	Intermediate Similarity	NPC229825
0.8478	Intermediate Similarity	NPC473330
0.8478	Intermediate Similarity	NPC473316
0.8478	Intermediate Similarity	NPC471147
0.8452	Intermediate Similarity	NPC93763
0.8452	Intermediate Similarity	NPC108816
0.8444	Intermediate Similarity	NPC166919
0.8438	Intermediate Similarity	NPC149371
0.8427	Intermediate Similarity	NPC179659
0.8427	Intermediate Similarity	NPC248602
0.8427	Intermediate Similarity	NPC160138
0.8427	Intermediate Similarity	NPC186148
0.8421	Intermediate Similarity	NPC475949
0.8409	Intermediate Similarity	NPC470755
0.8391	Intermediate Similarity	NPC11620
0.8391	Intermediate Similarity	NPC116543
0.8387	Intermediate Similarity	NPC471141
0.8372	Intermediate Similarity	NPC52861
0.8353	Intermediate Similarity	NPC89128
0.8353	Intermediate Similarity	NPC98557
0.8353	Intermediate Similarity	NPC167881
0.8352	Intermediate Similarity	NPC475748
0.8352	Intermediate Similarity	NPC251385
0.8352	Intermediate Similarity	NPC469368
0.8352	Intermediate Similarity	NPC49342
0.8333	Intermediate Similarity	NPC476805
0.8333	Intermediate Similarity	NPC47880
0.8333	Intermediate Similarity	NPC281516
0.8333	Intermediate Similarity	NPC475819
0.8333	Intermediate Similarity	NPC58219
0.8333	Intermediate Similarity	NPC177629
0.8316	Intermediate Similarity	NPC187268
0.8315	Intermediate Similarity	NPC50637
0.8315	Intermediate Similarity	NPC150755
0.8315	Intermediate Similarity	NPC112685
0.8315	Intermediate Similarity	NPC122502
0.8315	Intermediate Similarity	NPC164393
0.8298	Intermediate Similarity	NPC306041
0.8283	Intermediate Similarity	NPC477513
0.8265	Intermediate Similarity	NPC100487
0.8247	Intermediate Similarity	NPC471148
0.8242	Intermediate Similarity	NPC477011
0.8242	Intermediate Similarity	NPC92974
0.8235	Intermediate Similarity	NPC267231
0.8222	Intermediate Similarity	NPC475703
0.8214	Intermediate Similarity	NPC235906
0.8202	Intermediate Similarity	NPC100921
0.8202	Intermediate Similarity	NPC329749
0.8202	Intermediate Similarity	NPC477018
0.8202	Intermediate Similarity	NPC165162
0.8191	Intermediate Similarity	NPC304886
0.8191	Intermediate Similarity	NPC107476
0.8182	Intermediate Similarity	NPC59097
0.8182	Intermediate Similarity	NPC318468
0.8182	Intermediate Similarity	NPC170286
0.8182	Intermediate Similarity	NPC272814
0.8182	Intermediate Similarity	NPC243998
0.8172	Intermediate Similarity	NPC469692
0.8172	Intermediate Similarity	NPC475302
0.8172	Intermediate Similarity	NPC469645
0.8163	Intermediate Similarity	NPC475871
0.8163	Intermediate Similarity	NPC475945
0.8152	Intermediate Similarity	NPC80875
0.8144	Intermediate Similarity	NPC474742
0.8144	Intermediate Similarity	NPC474339
0.8144	Intermediate Similarity	NPC476270
0.8144	Intermediate Similarity	NPC164598
0.8144	Intermediate Similarity	NPC473332
0.8144	Intermediate Similarity	NPC201718
0.814	Intermediate Similarity	NPC86971
0.814	Intermediate Similarity	NPC470244
0.814	Intermediate Similarity	NPC470239
0.8125	Intermediate Similarity	NPC23364
0.8125	Intermediate Similarity	NPC279561
0.8118	Intermediate Similarity	NPC476028
0.8118	Intermediate Similarity	NPC171204
0.8118	Intermediate Similarity	NPC141789
0.8111	Intermediate Similarity	NPC114694
0.8111	Intermediate Similarity	NPC240695
0.8111	Intermediate Similarity	NPC231096
0.8111	Intermediate Similarity	NPC309211
0.8111	Intermediate Similarity	NPC232555
0.8111	Intermediate Similarity	NPC477010
0.8111	Intermediate Similarity	NPC107717
0.8111	Intermediate Similarity	NPC474949
0.8111	Intermediate Similarity	NPC171174
0.8111	Intermediate Similarity	NPC475019
0.8111	Intermediate Similarity	NPC142117
0.8111	Intermediate Similarity	NPC62118
0.8111	Intermediate Similarity	NPC475581
0.8095	Intermediate Similarity	NPC155587
0.809	Intermediate Similarity	NPC151176
0.809	Intermediate Similarity	NPC9868
0.809	Intermediate Similarity	NPC475963
0.809	Intermediate Similarity	NPC474776
0.809	Intermediate Similarity	NPC3464
0.8085	Intermediate Similarity	NPC140543
0.8085	Intermediate Similarity	NPC71589
0.8085	Intermediate Similarity	NPC190294
0.8085	Intermediate Similarity	NPC121825
0.8085	Intermediate Similarity	NPC474338
0.8081	Intermediate Similarity	NPC203659
0.8072	Intermediate Similarity	NPC58956
0.8072	Intermediate Similarity	NPC295633
0.8072	Intermediate Similarity	NPC269206
0.8065	Intermediate Similarity	NPC470373
0.8065	Intermediate Similarity	NPC70251
0.8065	Intermediate Similarity	NPC475881
0.8065	Intermediate Similarity	NPC470379
0.8061	Intermediate Similarity	NPC474747
0.8061	Intermediate Similarity	NPC324017

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 NPC474032 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1719
0.2-0.3	3670
0.3-0.4	2378
0.4-0.5	781
0.5-0.6	348
0.6-0.7	56
0.7-0.8	21
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
0.8621	High Similarity	NPD1733	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD6698	Approved
0.7957	Intermediate Similarity	NPD46	Approved
0.7872	Intermediate Similarity	NPD7983	Approved
0.7449	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5785	Approved
0.7396	Intermediate Similarity	NPD7838	Discovery
0.7391	Intermediate Similarity	NPD7154	Phase 3
0.7358	Intermediate Similarity	NPD6371	Approved
0.734	Intermediate Similarity	NPD5786	Approved
0.7245	Intermediate Similarity	NPD5779	Approved
0.7245	Intermediate Similarity	NPD5778	Approved
0.7234	Intermediate Similarity	NPD5363	Approved
0.7228	Intermediate Similarity	NPD4225	Approved
0.7204	Intermediate Similarity	NPD5362	Discontinued
0.7158	Intermediate Similarity	NPD4249	Approved
0.713	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1695	Approved
0.7097	Intermediate Similarity	NPD4269	Approved
0.7097	Intermediate Similarity	NPD4270	Approved
0.7083	Intermediate Similarity	NPD4251	Approved
0.7083	Intermediate Similarity	NPD4250	Approved
0.703	Intermediate Similarity	NPD7839	Suspended
0.7009	Intermediate Similarity	NPD6686	Approved
0.6915	Remote Similarity	NPD6435	Approved
0.6882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4252	Approved
0.6875	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8516	Approved
0.687	Remote Similarity	NPD8517	Approved
0.687	Remote Similarity	NPD8515	Approved
0.687	Remote Similarity	NPD8513	Phase 3
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7640	Approved
0.6827	Remote Similarity	NPD7639	Approved
0.6809	Remote Similarity	NPD5369	Approved
0.6762	Remote Similarity	NPD5344	Discontinued
0.6757	Remote Similarity	NPD6053	Discontinued
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7638	Approved
0.6702	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD4821	Approved
0.6702	Remote Similarity	NPD5368	Approved
0.6702	Remote Similarity	NPD4822	Approved
0.6702	Remote Similarity	NPD4819	Approved
0.6701	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD4268	Approved
0.6632	Remote Similarity	NPD4790	Discontinued
0.66	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8074	Phase 3
0.6522	Remote Similarity	NPD7115	Discovery
0.6509	Remote Similarity	NPD6648	Approved
0.6505	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD7637	Suspended
0.6437	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5370	Suspended
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5209	Approved
0.6383	Remote Similarity	NPD4756	Discovery
0.6344	Remote Similarity	NPD8039	Approved
0.6339	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7642	Approved
0.6333	Remote Similarity	NPD7829	Approved
0.6333	Remote Similarity	NPD7830	Approved
0.6325	Remote Similarity	NPD7641	Discontinued
0.6311	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6422	Discontinued
0.6283	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.624	Remote Similarity	NPD7260	Phase 2
0.6239	Remote Similarity	NPD7632	Discontinued
0.623	Remote Similarity	NPD7507	Approved
0.6216	Remote Similarity	NPD6008	Approved
0.618	Remote Similarity	NPD7331	Phase 2
0.6167	Remote Similarity	NPD8444	Approved
0.6136	Remote Similarity	NPD3197	Phase 1
0.6124	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6009	Approved
0.6102	Remote Similarity	NPD7500	Approved
0.6098	Remote Similarity	NPD8451	Approved
0.6087	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6319	Approved
0.608	Remote Similarity	NPD7319	Approved
0.6075	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6845	Suspended
0.6048	Remote Similarity	NPD8448	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.6033	Remote Similarity	NPD5983	Phase 2
0.6018	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5697	Approved
0.6018	Remote Similarity	NPD6412	Phase 2
0.6016	Remote Similarity	NPD8342	Approved
0.6016	Remote Similarity	NPD8341	Approved
0.6016	Remote Similarity	NPD8299	Approved
0.6016	Remote Similarity	NPD7492	Approved
0.6016	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD6421	Discontinued
0.5977	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8273	Phase 1
0.5968	Remote Similarity	NPD6616	Approved
0.5965	Remote Similarity	NPD6881	Approved
0.5965	Remote Similarity	NPD6899	Approved
0.5965	Remote Similarity	NPD6011	Approved
0.595	Remote Similarity	NPD6054	Approved
0.5948	Remote Similarity	NPD2204	Approved
0.5948	Remote Similarity	NPD6649	Approved
0.5948	Remote Similarity	NPD6650	Approved
0.5935	Remote Similarity	NPD7604	Phase 2
0.5929	Remote Similarity	NPD5739	Approved
0.5929	Remote Similarity	NPD6675	Approved
0.5929	Remote Similarity	NPD7128	Approved
0.5929	Remote Similarity	NPD5048	Discontinued
0.5929	Remote Similarity	NPD6402	Approved
0.5922	Remote Similarity	NPD7524	Approved
0.592	Remote Similarity	NPD7078	Approved
0.5913	Remote Similarity	NPD6373	Approved
0.5913	Remote Similarity	NPD6014	Approved
0.5913	Remote Similarity	NPD6372	Approved
0.5913	Remote Similarity	NPD6013	Approved
0.5913	Remote Similarity	NPD6012	Approved
0.5906	Remote Similarity	NPD8390	Approved
0.5906	Remote Similarity	NPD8391	Approved
0.5906	Remote Similarity	NPD8392	Approved
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD6016	Approved
0.59	Remote Similarity	NPD3667	Approved
0.59	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6647	Phase 2
0.5889	Remote Similarity	NPD7341	Phase 2
0.5888	Remote Similarity	NPD7748	Approved
0.5877	Remote Similarity	NPD5701	Approved
0.5873	Remote Similarity	NPD7736	Approved
0.5872	Remote Similarity	NPD7902	Approved
0.5872	Remote Similarity	NPD6083	Phase 2
0.5872	Remote Similarity	NPD6084	Phase 2
0.5862	Remote Similarity	NPD6883	Approved
0.5862	Remote Similarity	NPD7290	Approved
0.5862	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD2067	Discontinued
0.5854	Remote Similarity	NPD5988	Approved
0.5854	Remote Similarity	NPD6370	Approved
0.5849	Remote Similarity	NPD6079	Approved
0.5849	Remote Similarity	NPD7515	Phase 2
0.5842	Remote Similarity	NPD6695	Phase 3
0.584	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD5695	Phase 3
0.5826	Remote Similarity	NPD7320	Approved
0.5825	Remote Similarity	NPD7146	Approved
0.5825	Remote Similarity	NPD6409	Approved
0.5825	Remote Similarity	NPD7521	Approved
0.5825	Remote Similarity	NPD3618	Phase 1
0.5825	Remote Similarity	NPD6684	Approved
0.5825	Remote Similarity	NPD5330	Approved
0.5825	Remote Similarity	NPD7334	Approved
0.582	Remote Similarity	NPD6059	Approved
0.5818	Remote Similarity	NPD5696	Approved
0.5812	Remote Similarity	NPD8130	Phase 1
0.5812	Remote Similarity	NPD6847	Approved
0.5812	Remote Similarity	NPD6869	Approved
0.5812	Remote Similarity	NPD6617	Approved
0.581	Remote Similarity	NPD5328	Approved
0.5806	Remote Similarity	NPD8328	Phase 3
0.5804	Remote Similarity	NPD5211	Phase 2
0.5794	Remote Similarity	NPD8293	Discontinued
0.5784	Remote Similarity	NPD4786	Approved
0.5784	Remote Similarity	NPD3665	Phase 1
0.5784	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD3133	Approved
0.5784	Remote Similarity	NPD3666	Approved
0.578	Remote Similarity	NPD5222	Approved
0.578	Remote Similarity	NPD5221	Approved
0.578	Remote Similarity	NPD4697	Phase 3
0.578	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7909	Approved
0.5772	Remote Similarity	NPD8267	Approved
0.5772	Remote Similarity	NPD8266	Approved
0.5772	Remote Similarity	NPD8268	Approved
0.5772	Remote Similarity	NPD8269	Approved
0.5763	Remote Similarity	NPD6882	Approved
0.5728	Remote Similarity	NPD1696	Phase 3
0.5727	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD5737	Approved
0.5714	Remote Similarity	NPD8133	Approved
0.5714	Remote Similarity	NPD3172	Approved
0.5714	Remote Similarity	NPD6672	Approved
0.5714	Remote Similarity	NPD6903	Approved
0.5714	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5141	Approved
0.5702	Remote Similarity	NPD8137	Clinical (unspecified phase)

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