NPASS Compound

Structure

CID303777 OpenBabel06191716112D 35 39 0 0 1 0 0 0 0 0999 V2000 -0.0281 -2.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2780 2.8664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1221 2.3789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7992 -4.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2887 -3.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4581 -0.5026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8689 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6394 1.8918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0961 0.4719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2771 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8198 1.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6396 -2.8355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8190 -1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6377 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8207 -2.3636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -0.9461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4578 -2.3622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6380 -0.9451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4587 1.4185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0964 1.4181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8198 -1.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6389 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3074 -2.8517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2777 1.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3082 -3.8322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4584 0.4724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8196 0.4728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4828 -1.4338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9410 1.9052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1561 -2.3607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4595 -4.3232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4570 -1.4170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 30 1 0 0 0 0 16 1 1 1 0 0 0 16 23 1 0 0 0 0 17 23 2 0 0 0 0 17 30 1 0 0 0 0 18 24 1 0 0 0 0 18 31 1 6 0 0 0 19 25 1 6 0 0 0 19 35 1 0 0 0 0 20 15 1 6 0 0 0 20 23 1 0 0 0 0 20 35 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 25 27 1 0 0 0 0 25 33 1 1 0 0 0 27 34 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	523.332
LogP:	4.03
LogD:	3.201
LogS:	-4.049
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	5.399
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121
MDCK Permeability:	1.3393438166531269e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.78
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.114
30% Bioavailability (F30%):	0.81

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.481
Plasma Protein Binding (PPB):	89.41197967529297%
Volume Distribution (VD):	1.074
Pgp-substrate:	7.662017822265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.682

ADMET: Excretion

Clearance (CL):	7.631
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.179
Carcinogencity:	0.667
Eye Corrosion:	0.005
Eye Irritation:	0.013
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC303777

Natural Product ID:	NPC303777
*Common Name:**	YNKJSQIXVXWFBK-SLGDLKFASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YNKJSQIXVXWFBK-SLGDLKFASA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-16-13-19(25(33)27(4,5)34)35-20-15-30(8)17(23(16)20)14-18(31)24-28(6)11-10-22(32)26(2,3)21(28)9-12-29(24,30)7/h16,18-21,24-25,31,33-34H,9-15H2,1-8H3/t16-,18+,19+,20+,21+,24+,25-,28+,29+,30+/m1/s1
SMILES:	O[C@H]1CC2=C3[C@H](C)C[C@H](O[C@H]3C[C@@]2([C@@]2([C@@H]1[C@@]1(C)CCC(=O)C([C@@H]1CC2)(C)C)C)C)[C@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3121589
PubChem CID:	76310822
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10306	Alisma orienatale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	15100.0	nM	PMID[483571]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	600.0	nM	PMID[483570]

☑ 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 NPC303777 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	246
0.1-0.2	1541
0.2-0.3	4535
0.3-0.4	10212
0.4-0.5	12290
0.5-0.6	6206
0.6-0.7	5631
0.7-0.8	1954
0.8-0.85	61
0.85-0.9	15
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471784
0.9579	High Similarity	NPC324001
0.9468	High Similarity	NPC473176
0.913	High Similarity	NPC473166
0.9032	High Similarity	NPC274046
0.9032	High Similarity	NPC198074
0.8901	High Similarity	NPC469317
0.8901	High Similarity	NPC241875
0.8901	High Similarity	NPC469314
0.89	High Similarity	NPC473173
0.89	High Similarity	NPC469318
0.8842	High Similarity	NPC37787
0.8842	High Similarity	NPC30677
0.8842	High Similarity	NPC180557
0.8842	High Similarity	NPC473415
0.8842	High Similarity	NPC469329
0.8776	High Similarity	NPC473174
0.8713	High Similarity	NPC144459
0.871	High Similarity	NPC469323
0.8687	High Similarity	NPC469316
0.8586	High Similarity	NPC476897
0.8557	High Similarity	NPC471777
0.8542	High Similarity	NPC240617
0.8511	High Similarity	NPC469319
0.8511	High Similarity	NPC229871
0.85	High Similarity	NPC185530
0.8495	Intermediate Similarity	NPC469322
0.8462	Intermediate Similarity	NPC86370
0.8416	Intermediate Similarity	NPC26478
0.835	Intermediate Similarity	NPC471783
0.835	Intermediate Similarity	NPC9457
0.835	Intermediate Similarity	NPC473165
0.8333	Intermediate Similarity	NPC149124
0.8333	Intermediate Similarity	NPC75531
0.8333	Intermediate Similarity	NPC473167
0.8333	Intermediate Similarity	NPC473175
0.8252	Intermediate Similarity	NPC60681
0.8218	Intermediate Similarity	NPC469327
0.8182	Intermediate Similarity	NPC471822
0.8173	Intermediate Similarity	NPC131665
0.8173	Intermediate Similarity	NPC255387
0.8148	Intermediate Similarity	NPC284915
0.8131	Intermediate Similarity	NPC470063
0.81	Intermediate Similarity	NPC175351
0.81	Intermediate Similarity	NPC121402
0.81	Intermediate Similarity	NPC132753
0.81	Intermediate Similarity	NPC151681
0.81	Intermediate Similarity	NPC224356
0.81	Intermediate Similarity	NPC474977
0.8095	Intermediate Similarity	NPC177064
0.8081	Intermediate Similarity	NPC473170
0.8077	Intermediate Similarity	NPC470587
0.8077	Intermediate Similarity	NPC173172
0.8077	Intermediate Similarity	NPC475414
0.8061	Intermediate Similarity	NPC141447
0.8058	Intermediate Similarity	NPC239716
0.8041	Intermediate Similarity	NPC472307
0.8019	Intermediate Similarity	NPC472216
0.8019	Intermediate Similarity	NPC475065
0.8019	Intermediate Similarity	NPC284828
0.8019	Intermediate Similarity	NPC173905
0.8019	Intermediate Similarity	NPC41405
0.8019	Intermediate Similarity	NPC5475
0.8	Intermediate Similarity	NPC470493
0.8	Intermediate Similarity	NPC472363
0.8	Intermediate Similarity	NPC312824
0.8	Intermediate Similarity	NPC301666
0.8	Intermediate Similarity	NPC330011
0.8	Intermediate Similarity	NPC471737
0.8	Intermediate Similarity	NPC329048
0.8	Intermediate Similarity	NPC475176
0.8	Intermediate Similarity	NPC472362
0.8	Intermediate Similarity	NPC183580
0.8	Intermediate Similarity	NPC154526
0.7979	Intermediate Similarity	NPC473157
0.7963	Intermediate Similarity	NPC476163
0.7961	Intermediate Similarity	NPC165250
0.7941	Intermediate Similarity	NPC83709
0.7938	Intermediate Similarity	NPC77263
0.7938	Intermediate Similarity	NPC250592
0.7938	Intermediate Similarity	NPC32830
0.7925	Intermediate Similarity	NPC473482
0.7925	Intermediate Similarity	NPC475418
0.7925	Intermediate Similarity	NPC318363
0.7921	Intermediate Similarity	NPC474938
0.7921	Intermediate Similarity	NPC474785
0.7917	Intermediate Similarity	NPC138756
0.7905	Intermediate Similarity	NPC478052
0.7905	Intermediate Similarity	NPC472655
0.7885	Intermediate Similarity	NPC112009
0.7885	Intermediate Similarity	NPC471005
0.7879	Intermediate Similarity	NPC469315
0.7864	Intermediate Similarity	NPC235142
0.7857	Intermediate Similarity	NPC42673
0.7857	Intermediate Similarity	NPC230513
0.7857	Intermediate Similarity	NPC264954
0.7843	Intermediate Similarity	NPC470068
0.7838	Intermediate Similarity	NPC167606
0.7838	Intermediate Similarity	NPC55296
0.7838	Intermediate Similarity	NPC470492
0.7838	Intermediate Similarity	NPC140055
0.7838	Intermediate Similarity	NPC286528
0.7838	Intermediate Similarity	NPC20302
0.783	Intermediate Similarity	NPC67321
0.783	Intermediate Similarity	NPC187435
0.7822	Intermediate Similarity	NPC160056
0.7818	Intermediate Similarity	NPC147912
0.7818	Intermediate Similarity	NPC472274
0.7818	Intermediate Similarity	NPC477580
0.7818	Intermediate Similarity	NPC67259
0.7818	Intermediate Similarity	NPC475163
0.781	Intermediate Similarity	NPC222161
0.78	Intermediate Similarity	NPC67831
0.78	Intermediate Similarity	NPC91010
0.78	Intermediate Similarity	NPC174051
0.7788	Intermediate Similarity	NPC114540
0.7788	Intermediate Similarity	NPC251226
0.7788	Intermediate Similarity	NPC474370
0.7788	Intermediate Similarity	NPC268530
0.7788	Intermediate Similarity	NPC155332
0.7788	Intermediate Similarity	NPC154491
0.7788	Intermediate Similarity	NPC32577
0.7778	Intermediate Similarity	NPC475563
0.7778	Intermediate Similarity	NPC470065
0.7778	Intermediate Similarity	NPC29133
0.7778	Intermediate Similarity	NPC475134
0.7778	Intermediate Similarity	NPC262870
0.7778	Intermediate Similarity	NPC155304
0.7778	Intermediate Similarity	NPC235704
0.7768	Intermediate Similarity	NPC50774
0.7768	Intermediate Similarity	NPC186525
0.7768	Intermediate Similarity	NPC709
0.7767	Intermediate Similarity	NPC473510
0.7757	Intermediate Similarity	NPC306265
0.7755	Intermediate Similarity	NPC122116
0.7748	Intermediate Similarity	NPC64318
0.7745	Intermediate Similarity	NPC291634
0.7745	Intermediate Similarity	NPC272451
0.7745	Intermediate Similarity	NPC210337
0.7745	Intermediate Similarity	NPC126815
0.7732	Intermediate Similarity	NPC90652
0.7727	Intermediate Similarity	NPC255017
0.7719	Intermediate Similarity	NPC470878
0.7719	Intermediate Similarity	NPC4021
0.7719	Intermediate Similarity	NPC473256
0.7719	Intermediate Similarity	NPC159456
0.7714	Intermediate Similarity	NPC471208
0.7714	Intermediate Similarity	NPC168575
0.7714	Intermediate Similarity	NPC180204
0.7714	Intermediate Similarity	NPC264048
0.7714	Intermediate Similarity	NPC194323
0.7708	Intermediate Similarity	NPC197823
0.7706	Intermediate Similarity	NPC475480
0.7706	Intermediate Similarity	NPC473921
0.7706	Intermediate Similarity	NPC470961
0.7706	Intermediate Similarity	NPC475668
0.77	Intermediate Similarity	NPC307776
0.77	Intermediate Similarity	NPC27918
0.7699	Intermediate Similarity	NPC473274
0.7699	Intermediate Similarity	NPC473270
0.7699	Intermediate Similarity	NPC477071
0.7699	Intermediate Similarity	NPC475041
0.7692	Intermediate Similarity	NPC233012
0.7692	Intermediate Similarity	NPC470054
0.7692	Intermediate Similarity	NPC54909
0.7692	Intermediate Similarity	NPC303559
0.7685	Intermediate Similarity	NPC218853
0.7679	Intermediate Similarity	NPC470959
0.7679	Intermediate Similarity	NPC473590
0.7679	Intermediate Similarity	NPC476965
0.7677	Intermediate Similarity	NPC85173
0.7677	Intermediate Similarity	NPC161638
0.7677	Intermediate Similarity	NPC136801
0.7672	Intermediate Similarity	NPC469790
0.767	Intermediate Similarity	NPC476895
0.767	Intermediate Similarity	NPC124703
0.767	Intermediate Similarity	NPC234617
0.7664	Intermediate Similarity	NPC473169
0.7664	Intermediate Similarity	NPC473284
0.7653	Intermediate Similarity	NPC230387
0.7653	Intermediate Similarity	NPC193360
0.7653	Intermediate Similarity	NPC474677
0.7653	Intermediate Similarity	NPC470417
0.7652	Intermediate Similarity	NPC88326
0.7652	Intermediate Similarity	NPC153700
0.7647	Intermediate Similarity	NPC230151
0.7647	Intermediate Similarity	NPC117133
0.7647	Intermediate Similarity	NPC88009
0.7647	Intermediate Similarity	NPC91439
0.7647	Intermediate Similarity	NPC235053
0.7642	Intermediate Similarity	NPC294259
0.7642	Intermediate Similarity	NPC137657
0.7636	Intermediate Similarity	NPC191620
0.7636	Intermediate Similarity	NPC207251
0.7629	Intermediate Similarity	NPC213412
0.7629	Intermediate Similarity	NPC56588
0.7624	Intermediate Similarity	NPC318332
0.7624	Intermediate Similarity	NPC471720
0.7624	Intermediate Similarity	NPC474690
0.7624	Intermediate Similarity	NPC472976

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 NPC303777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1846
0.2-0.3	3731
0.3-0.4	2234
0.4-0.5	701
0.5-0.6	212
0.6-0.7	186
0.7-0.8	23
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
0.7838	Intermediate Similarity	NPD7115	Discovery
0.7523	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD7507	Approved
0.7429	Intermediate Similarity	NPD7640	Approved
0.7429	Intermediate Similarity	NPD7639	Approved
0.7423	Intermediate Similarity	NPD4786	Approved
0.7396	Intermediate Similarity	NPD3667	Approved
0.7339	Intermediate Similarity	NPD6412	Phase 2
0.7333	Intermediate Similarity	NPD4225	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD7319	Approved
0.7255	Intermediate Similarity	NPD7515	Phase 2
0.7248	Intermediate Similarity	NPD7128	Approved
0.7248	Intermediate Similarity	NPD6675	Approved
0.7248	Intermediate Similarity	NPD6402	Approved
0.7248	Intermediate Similarity	NPD5739	Approved
0.7238	Intermediate Similarity	NPD4755	Approved
0.7228	Intermediate Similarity	NPD5328	Approved
0.7207	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4159	Approved
0.7184	Intermediate Similarity	NPD4202	Approved
0.7184	Intermediate Similarity	NPD6399	Phase 3
0.7172	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8297	Approved
0.7155	Intermediate Similarity	NPD7328	Approved
0.7155	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5211	Phase 2
0.7119	Intermediate Similarity	NPD8033	Approved
0.7117	Intermediate Similarity	NPD7320	Approved
0.7117	Intermediate Similarity	NPD6899	Approved
0.7117	Intermediate Similarity	NPD6881	Approved
0.7117	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6686	Approved
0.7105	Intermediate Similarity	NPD8133	Approved
0.7103	Intermediate Similarity	NPD5285	Approved
0.7103	Intermediate Similarity	NPD4700	Approved
0.7103	Intermediate Similarity	NPD5286	Approved
0.7103	Intermediate Similarity	NPD4696	Approved
0.7094	Intermediate Similarity	NPD7516	Approved
0.7087	Intermediate Similarity	NPD6079	Approved
0.7087	Intermediate Similarity	NPD8034	Phase 2
0.7087	Intermediate Similarity	NPD8035	Phase 2
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD3665	Phase 1
0.7071	Intermediate Similarity	NPD3666	Approved
0.7071	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD4753	Phase 2
0.7054	Intermediate Similarity	NPD6373	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7034	Intermediate Similarity	NPD8377	Approved
0.7034	Intermediate Similarity	NPD8294	Approved
0.7027	Intermediate Similarity	NPD5701	Approved
0.7027	Intermediate Similarity	NPD5697	Approved
0.701	Intermediate Similarity	NPD7525	Registered
0.7	Intermediate Similarity	NPD5141	Approved
0.6991	Remote Similarity	NPD7102	Approved
0.6991	Remote Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD7290	Approved
0.6975	Remote Similarity	NPD8379	Approved
0.6975	Remote Similarity	NPD8296	Approved
0.6975	Remote Similarity	NPD8378	Approved
0.6975	Remote Similarity	NPD8335	Approved
0.6975	Remote Similarity	NPD8380	Approved
0.6972	Remote Similarity	NPD4633	Approved
0.6972	Remote Similarity	NPD5224	Approved
0.6972	Remote Similarity	NPD5225	Approved
0.6972	Remote Similarity	NPD5226	Approved
0.697	Remote Similarity	NPD4788	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8130	Phase 1
0.693	Remote Similarity	NPD6869	Approved
0.693	Remote Similarity	NPD6847	Approved
0.693	Remote Similarity	NPD6617	Approved
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5174	Approved
0.6909	Remote Similarity	NPD5175	Approved
0.6907	Remote Similarity	NPD7645	Phase 2
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6014	Approved
0.69	Remote Similarity	NPD3668	Phase 3
0.6882	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6882	Approved
0.6848	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4634	Approved
0.6822	Remote Similarity	NPD4697	Phase 3
0.6822	Remote Similarity	NPD5221	Approved
0.6822	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5222	Approved
0.6814	Remote Similarity	NPD6011	Approved
0.681	Remote Similarity	NPD4632	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4768	Approved
0.6786	Remote Similarity	NPD4767	Approved
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4244	Approved
0.6774	Remote Similarity	NPD4245	Approved
0.6771	Remote Similarity	NPD6117	Approved
0.6765	Remote Similarity	NPD6684	Approved
0.6765	Remote Similarity	NPD7334	Approved
0.6765	Remote Similarity	NPD7146	Approved
0.6765	Remote Similarity	NPD6409	Approved
0.6765	Remote Similarity	NPD5330	Approved
0.6765	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD5173	Approved
0.6757	Remote Similarity	NPD4754	Approved
0.675	Remote Similarity	NPD6319	Approved
0.675	Remote Similarity	NPD6059	Approved
0.675	Remote Similarity	NPD6054	Approved
0.6729	Remote Similarity	NPD5695	Phase 3
0.6729	Remote Similarity	NPD5210	Approved
0.6729	Remote Similarity	NPD4629	Approved
0.6701	Remote Similarity	NPD6116	Phase 1
0.67	Remote Similarity	NPD4221	Approved
0.67	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD7524	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD3698	Phase 2
0.664	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6635	Remote Similarity	NPD6903	Approved
0.6633	Remote Similarity	NPD6114	Approved
0.6633	Remote Similarity	NPD3617	Approved
0.6633	Remote Similarity	NPD6115	Approved
0.6633	Remote Similarity	NPD6697	Approved
0.6633	Remote Similarity	NPD6118	Approved
0.6604	Remote Similarity	NPD6411	Approved
0.6604	Remote Similarity	NPD5693	Phase 1
0.6602	Remote Similarity	NPD4623	Approved
0.6602	Remote Similarity	NPD4519	Discontinued
0.66	Remote Similarity	NPD4139	Approved
0.66	Remote Similarity	NPD4692	Approved
0.6598	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8328	Phase 3
0.6574	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6051	Approved
0.6569	Remote Similarity	NPD4197	Approved
0.6562	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5360	Phase 3
0.6557	Remote Similarity	NPD6015	Approved
0.6557	Remote Similarity	NPD6016	Approved
0.6555	Remote Similarity	NPD6274	Approved
0.6552	Remote Similarity	NPD5249	Phase 3
0.6552	Remote Similarity	NPD6371	Approved
0.6552	Remote Similarity	NPD5250	Approved
0.6552	Remote Similarity	NPD5248	Approved
0.6552	Remote Similarity	NPD5251	Approved
0.6552	Remote Similarity	NPD5247	Approved
0.6549	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7492	Approved
0.6529	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD7100	Approved
0.6509	Remote Similarity	NPD6698	Approved
0.6509	Remote Similarity	NPD46	Approved
0.6505	Remote Similarity	NPD1694	Approved
0.6504	Remote Similarity	NPD5988	Approved
0.65	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD4748	Discontinued
0.6496	Remote Similarity	NPD5217	Approved
0.6496	Remote Similarity	NPD5216	Approved
0.6496	Remote Similarity	NPD5215	Approved
0.6495	Remote Similarity	NPD7339	Approved
0.6495	Remote Similarity	NPD6942	Approved
0.6491	Remote Similarity	NPD6008	Approved
0.648	Remote Similarity	NPD6616	Approved
0.6476	Remote Similarity	NPD6672	Approved
0.6476	Remote Similarity	NPD5737	Approved
0.6471	Remote Similarity	NPD6695	Phase 3
0.6452	Remote Similarity	NPD7604	Phase 2
0.6446	Remote Similarity	NPD6335	Approved
0.6442	Remote Similarity	NPD5205	Approved
0.6442	Remote Similarity	NPD4138	Approved
0.6442	Remote Similarity	NPD6098	Approved
0.6442	Remote Similarity	NPD4690	Approved
0.6442	Remote Similarity	NPD5279	Phase 3
0.6442	Remote Similarity	NPD4693	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