NPASS Compound

Structure

NPC185553 OpenBabel07101718222D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.9481 1.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 -5.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2611 -2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -6.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9624 -1.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0928 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4722 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5636 0.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 0.6683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8825 -4.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3476 -1.5231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7187 -5.3088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1311 -0.0865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9616 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7451 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1765 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0464 -1.4468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8825 -3.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3795 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9163 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5549 -4.8261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8317 -2.4847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3208 -1.1027 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 -2.0464 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 2 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 3 1 6 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 4 1 1 0 0 0 12 21 1 0 0 0 0 13 20 1 1 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	0.874
LogD:	0.594
LogS:	-2.279
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	5.074
Fsp3:	0.65
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:	-4.707
MDCK Permeability:	2.772028346953448e-05
Pgp-inhibitor:	0.831
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.165
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.795
Plasma Protein Binding (PPB):	62.32815933227539%
Volume Distribution (VD):	1.111
Pgp-substrate:	37.327178955078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	5.813
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.766
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.634
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.395
Carcinogencity:	0.352
Eye Corrosion:	0.045
Eye Irritation:	0.209
Respiratory Toxicity:	0.863

Download Data

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

Natural Product: NPC185553

Natural Product ID:	NPC185553
*Common Name:**	11Alpha,13-Dihydrohelenalin-[2-(1-Hydroxyethyl)Acrylate]
IUPAC Name:	[(1R,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] (3R)-3-hydroxy-2-methylidenebutanoate
Synonyms:
Standard InCHIKey:	WFHQGSWLRAMECY-JTAIKEJBSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-9-8-14-16(11(3)19(24)25-14)17(26-18(23)10(2)12(4)21)20(5)13(9)6-7-15(20)22/h6-7,9,11-14,16-17,21H,2,8H2,1,3-5H3/t9-,11-,12-,13+,14-,16-,17+,20+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@H]([C@@H](C)C(=O)O2)[C@@H]([C@@]2(C)[C@H]1C=CC2=O)OC(=O)C(=C)[C@@H](C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514736
PubChem CID:	44583940
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
NPO24121	Vernoniopsis caudata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15921436]
NPO24121	Vernoniopsis caudata	n.a.	n.a.	n.a.	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	50.0	nM	PMID[459998]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	410.0	nM	PMID[459998]

☑ 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 NPC185553 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	210
0.1-0.2	1208
0.2-0.3	5142
0.3-0.4	10297
0.4-0.5	13064
0.5-0.6	7067
0.6-0.7	4622
0.7-0.8	980
0.8-0.85	63
0.85-0.9	22
0.9-0.95	15
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC169205
0.978	High Similarity	NPC141191
0.9667	High Similarity	NPC48803
0.9667	High Similarity	NPC90121
0.9667	High Similarity	NPC275960
0.9667	High Similarity	NPC193645
0.9438	High Similarity	NPC253144
0.9333	High Similarity	NPC70595
0.9333	High Similarity	NPC123177
0.9333	High Similarity	NPC74103
0.9333	High Similarity	NPC150978
0.9333	High Similarity	NPC284185
0.9326	High Similarity	NPC117405
0.9326	High Similarity	NPC52198
0.9263	High Similarity	NPC225353
0.9167	High Similarity	NPC110989
0.913	High Similarity	NPC167219
0.9072	High Similarity	NPC203659
0.8989	High Similarity	NPC70555
0.8989	High Similarity	NPC70422
0.8989	High Similarity	NPC104961
0.8925	High Similarity	NPC289004
0.8913	High Similarity	NPC111114
0.8913	High Similarity	NPC261607
0.8913	High Similarity	NPC300312
0.875	High Similarity	NPC54843
0.8696	High Similarity	NPC12872
0.8696	High Similarity	NPC168679
0.8667	High Similarity	NPC161957
0.8667	High Similarity	NPC33570
0.8667	High Similarity	NPC21471
0.8632	High Similarity	NPC304886
0.8602	High Similarity	NPC129419
0.8571	High Similarity	NPC171759
0.8571	High Similarity	NPC477950
0.8495	Intermediate Similarity	NPC268298
0.8485	Intermediate Similarity	NPC474747
0.8444	Intermediate Similarity	NPC39588
0.84	Intermediate Similarity	NPC475871
0.84	Intermediate Similarity	NPC475945
0.837	Intermediate Similarity	NPC238593
0.8351	Intermediate Similarity	NPC91771
0.8351	Intermediate Similarity	NPC142529
0.8351	Intermediate Similarity	NPC126156
0.8333	Intermediate Similarity	NPC469632
0.8317	Intermediate Similarity	NPC309190
0.8317	Intermediate Similarity	NPC100487
0.828	Intermediate Similarity	NPC237540
0.8265	Intermediate Similarity	NPC170143
0.8265	Intermediate Similarity	NPC213947
0.8265	Intermediate Similarity	NPC108475
0.8261	Intermediate Similarity	NPC165162
0.8261	Intermediate Similarity	NPC125290
0.8242	Intermediate Similarity	NPC215294
0.8229	Intermediate Similarity	NPC135776
0.8211	Intermediate Similarity	NPC145666
0.8211	Intermediate Similarity	NPC71533
0.8211	Intermediate Similarity	NPC106510
0.8211	Intermediate Similarity	NPC469368
0.82	Intermediate Similarity	NPC110443
0.82	Intermediate Similarity	NPC133907
0.82	Intermediate Similarity	NPC46998
0.82	Intermediate Similarity	NPC128733
0.82	Intermediate Similarity	NPC474742
0.82	Intermediate Similarity	NPC185141
0.8191	Intermediate Similarity	NPC476805
0.8172	Intermediate Similarity	NPC475461
0.8172	Intermediate Similarity	NPC107787
0.8172	Intermediate Similarity	NPC236692
0.8172	Intermediate Similarity	NPC305475
0.8172	Intermediate Similarity	NPC309757
0.8152	Intermediate Similarity	NPC165287
0.8152	Intermediate Similarity	NPC115786
0.8144	Intermediate Similarity	NPC477131
0.8144	Intermediate Similarity	NPC198853
0.8137	Intermediate Similarity	NPC474741
0.8125	Intermediate Similarity	NPC131209
0.8125	Intermediate Similarity	NPC133698
0.8111	Intermediate Similarity	NPC223904
0.8105	Intermediate Similarity	NPC295312
0.8085	Intermediate Similarity	NPC201658
0.8085	Intermediate Similarity	NPC72513
0.8081	Intermediate Similarity	NPC474343
0.8081	Intermediate Similarity	NPC477949
0.8065	Intermediate Similarity	NPC78089
0.8065	Intermediate Similarity	NPC470755
0.8065	Intermediate Similarity	NPC255307
0.8065	Intermediate Similarity	NPC261380
0.8058	Intermediate Similarity	NPC243998
0.8043	Intermediate Similarity	NPC54468
0.8041	Intermediate Similarity	NPC153590
0.8041	Intermediate Similarity	NPC308656
0.8041	Intermediate Similarity	NPC473234
0.8041	Intermediate Similarity	NPC60386
0.8041	Intermediate Similarity	NPC469645
0.8041	Intermediate Similarity	NPC200237
0.8041	Intermediate Similarity	NPC473263
0.8041	Intermediate Similarity	NPC473273
0.8041	Intermediate Similarity	NPC469692
0.8041	Intermediate Similarity	NPC475302
0.8039	Intermediate Similarity	NPC475873
0.8039	Intermediate Similarity	NPC472755
0.8037	Intermediate Similarity	NPC209058
0.8022	Intermediate Similarity	NPC470241
0.8021	Intermediate Similarity	NPC473455
0.8021	Intermediate Similarity	NPC77337
0.8021	Intermediate Similarity	NPC19087
0.802	Intermediate Similarity	NPC469657
0.802	Intermediate Similarity	NPC244456
0.802	Intermediate Similarity	NPC472753
0.8	Intermediate Similarity	NPC47951
0.8	Intermediate Similarity	NPC476803
0.798	Intermediate Similarity	NPC184065
0.798	Intermediate Similarity	NPC18019
0.798	Intermediate Similarity	NPC24956
0.7979	Intermediate Similarity	NPC150755
0.7959	Intermediate Similarity	NPC323008
0.7959	Intermediate Similarity	NPC65829
0.7959	Intermediate Similarity	NPC53685
0.7959	Intermediate Similarity	NPC470010
0.7959	Intermediate Similarity	NPC121825
0.7959	Intermediate Similarity	NPC473331
0.7959	Intermediate Similarity	NPC470013
0.7959	Intermediate Similarity	NPC262133
0.7957	Intermediate Similarity	NPC141193
0.7957	Intermediate Similarity	NPC114979
0.7957	Intermediate Similarity	NPC96259
0.7957	Intermediate Similarity	NPC476804
0.7957	Intermediate Similarity	NPC191476
0.7957	Intermediate Similarity	NPC158756
0.7944	Intermediate Similarity	NPC76550
0.7944	Intermediate Similarity	NPC138757
0.7944	Intermediate Similarity	NPC123855
0.7941	Intermediate Similarity	NPC86077
0.7941	Intermediate Similarity	NPC472754
0.7938	Intermediate Similarity	NPC286341
0.7938	Intermediate Similarity	NPC177037
0.7938	Intermediate Similarity	NPC472814
0.7938	Intermediate Similarity	NPC191339
0.7938	Intermediate Similarity	NPC475925
0.7938	Intermediate Similarity	NPC184063
0.7935	Intermediate Similarity	NPC89555
0.7925	Intermediate Similarity	NPC257240
0.7921	Intermediate Similarity	NPC288876
0.7917	Intermediate Similarity	NPC38392
0.7917	Intermediate Similarity	NPC87306
0.7917	Intermediate Similarity	NPC32922
0.7912	Intermediate Similarity	NPC74673
0.7912	Intermediate Similarity	NPC69271
0.79	Intermediate Similarity	NPC53844
0.7885	Intermediate Similarity	NPC223450
0.7879	Intermediate Similarity	NPC471142
0.7879	Intermediate Similarity	NPC214694
0.787	Intermediate Similarity	NPC46269
0.787	Intermediate Similarity	NPC106395
0.7857	Intermediate Similarity	NPC295204
0.7857	Intermediate Similarity	NPC475912
0.7857	Intermediate Similarity	NPC273579
0.7857	Intermediate Similarity	NPC288240
0.7857	Intermediate Similarity	NPC162205
0.7857	Intermediate Similarity	NPC115021
0.7849	Intermediate Similarity	NPC131669
0.7849	Intermediate Similarity	NPC169575
0.7849	Intermediate Similarity	NPC473390
0.7849	Intermediate Similarity	NPC40746
0.7843	Intermediate Similarity	NPC206079
0.7843	Intermediate Similarity	NPC47880
0.7835	Intermediate Similarity	NPC51486
0.7835	Intermediate Similarity	NPC179394
0.7835	Intermediate Similarity	NPC297474
0.7835	Intermediate Similarity	NPC475855
0.7835	Intermediate Similarity	NPC144133
0.7835	Intermediate Similarity	NPC473448
0.7835	Intermediate Similarity	NPC62815
0.7835	Intermediate Similarity	NPC54065
0.7826	Intermediate Similarity	NPC39411
0.7826	Intermediate Similarity	NPC301477
0.7826	Intermediate Similarity	NPC10276
0.7826	Intermediate Similarity	NPC35089
0.7826	Intermediate Similarity	NPC281949
0.7826	Intermediate Similarity	NPC255580
0.7826	Intermediate Similarity	NPC25684
0.7822	Intermediate Similarity	NPC64742
0.7822	Intermediate Similarity	NPC316598
0.7812	Intermediate Similarity	NPC469631
0.7812	Intermediate Similarity	NPC475906
0.7812	Intermediate Similarity	NPC475819
0.7812	Intermediate Similarity	NPC217983
0.7812	Intermediate Similarity	NPC469628
0.7812	Intermediate Similarity	NPC202672
0.7812	Intermediate Similarity	NPC207114
0.7812	Intermediate Similarity	NPC469653
0.7812	Intermediate Similarity	NPC471047
0.7802	Intermediate Similarity	NPC470239
0.7802	Intermediate Similarity	NPC470244
0.78	Intermediate Similarity	NPC242848
0.78	Intermediate Similarity	NPC230800
0.78	Intermediate Similarity	NPC9812
0.78	Intermediate Similarity	NPC476009
0.7798	Intermediate Similarity	NPC133677

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 NPC185553 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1812
0.2-0.3	3805
0.3-0.4	2252
0.4-0.5	647
0.5-0.6	284
0.6-0.7	137
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9667	High Similarity	NPD1698	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD5785	Approved
0.7925	Intermediate Similarity	NPD6371	Approved
0.7642	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5282	Discontinued
0.75	Intermediate Similarity	NPD5363	Approved
0.7476	Intermediate Similarity	NPD4225	Approved
0.7423	Intermediate Similarity	NPD5786	Approved
0.7374	Intermediate Similarity	NPD1695	Approved
0.7368	Intermediate Similarity	NPD5209	Approved
0.7368	Intermediate Similarity	NPD6435	Approved
0.732	Intermediate Similarity	NPD1694	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7188	Intermediate Similarity	NPD4269	Approved
0.7188	Intermediate Similarity	NPD4270	Approved
0.7158	Intermediate Similarity	NPD5368	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7128	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7154	Phase 3
0.7113	Intermediate Similarity	NPD5362	Discontinued
0.7083	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD7983	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5697	Approved
0.6979	Remote Similarity	NPD4252	Approved
0.6937	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD6650	Approved
0.6903	Remote Similarity	NPD6649	Approved
0.6875	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD6012	Approved
0.6875	Remote Similarity	NPD6013	Approved
0.6814	Remote Similarity	NPD7102	Approved
0.6814	Remote Similarity	NPD6883	Approved
0.6814	Remote Similarity	NPD7290	Approved
0.6804	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6698	Approved
0.6796	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD5211	Phase 2
0.6786	Remote Similarity	NPD6686	Approved
0.6786	Remote Similarity	NPD6011	Approved
0.6786	Remote Similarity	NPD7320	Approved
0.6757	Remote Similarity	NPD6675	Approved
0.6757	Remote Similarity	NPD7128	Approved
0.6757	Remote Similarity	NPD6402	Approved
0.6757	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6869	Approved
0.6754	Remote Similarity	NPD6847	Approved
0.6754	Remote Similarity	NPD6617	Approved
0.6754	Remote Similarity	NPD8130	Phase 1
0.6733	Remote Similarity	NPD4249	Approved
0.6726	Remote Similarity	NPD6373	Approved
0.6726	Remote Similarity	NPD6372	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6696	Remote Similarity	NPD8297	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6636	Remote Similarity	NPD7839	Suspended
0.6635	Remote Similarity	NPD7838	Discovery
0.6633	Remote Similarity	NPD4822	Approved
0.6633	Remote Similarity	NPD4819	Approved
0.6633	Remote Similarity	NPD4821	Approved
0.6633	Remote Similarity	NPD4820	Approved
0.6606	Remote Similarity	NPD7640	Approved
0.6606	Remote Similarity	NPD7639	Approved
0.6606	Remote Similarity	NPD4696	Approved
0.6606	Remote Similarity	NPD5286	Approved
0.6606	Remote Similarity	NPD5285	Approved
0.6598	Remote Similarity	NPD4268	Approved
0.6598	Remote Similarity	NPD4271	Approved
0.6585	Remote Similarity	NPD6616	Approved
0.6583	Remote Similarity	NPD6319	Approved
0.6583	Remote Similarity	NPD6054	Approved
0.6574	Remote Similarity	NPD6084	Phase 2
0.6574	Remote Similarity	NPD6083	Phase 2
0.6574	Remote Similarity	NPD7902	Approved
0.6571	Remote Similarity	NPD6079	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6542	Remote Similarity	NPD5695	Phase 3
0.6532	Remote Similarity	NPD7078	Approved
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6015	Approved
0.6529	Remote Similarity	NPD6016	Approved
0.6514	Remote Similarity	NPD7638	Approved
0.6514	Remote Similarity	NPD5696	Approved
0.6491	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5224	Approved
0.6486	Remote Similarity	NPD4633	Approved
0.6486	Remote Similarity	NPD5225	Approved
0.6486	Remote Similarity	NPD5226	Approved
0.6481	Remote Similarity	NPD5222	Approved
0.6481	Remote Similarity	NPD5221	Approved
0.6481	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7736	Approved
0.6475	Remote Similarity	NPD6370	Approved
0.6475	Remote Similarity	NPD5988	Approved
0.646	Remote Similarity	NPD6008	Approved
0.6449	Remote Similarity	NPD7748	Approved
0.6442	Remote Similarity	NPD6903	Approved
0.6436	Remote Similarity	NPD5331	Approved
0.6436	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD5174	Approved
0.6429	Remote Similarity	NPD5175	Approved
0.6422	Remote Similarity	NPD5173	Approved
0.6422	Remote Similarity	NPD4755	Approved
0.6415	Remote Similarity	NPD5284	Approved
0.6415	Remote Similarity	NPD7515	Phase 2
0.6415	Remote Similarity	NPD5281	Approved
0.6408	Remote Similarity	NPD6409	Approved
0.6408	Remote Similarity	NPD7334	Approved
0.6408	Remote Similarity	NPD7146	Approved
0.6408	Remote Similarity	NPD3618	Phase 1
0.6408	Remote Similarity	NPD7521	Approved
0.6408	Remote Similarity	NPD6684	Approved
0.6408	Remote Similarity	NPD5330	Approved
0.64	Remote Similarity	NPD4790	Discontinued
0.6396	Remote Similarity	NPD5223	Approved
0.6393	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD8515	Approved
0.6393	Remote Similarity	NPD8516	Approved
0.6393	Remote Similarity	NPD8513	Phase 3
0.6389	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD5210	Approved
0.6387	Remote Similarity	NPD6274	Approved
0.6381	Remote Similarity	NPD5328	Approved
0.6381	Remote Similarity	NPD5370	Suspended
0.6379	Remote Similarity	NPD4634	Approved
0.6373	Remote Similarity	NPD3666	Approved
0.6373	Remote Similarity	NPD3665	Phase 1
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7100	Approved
0.6364	Remote Similarity	NPD7101	Approved
0.6356	Remote Similarity	NPD4632	Approved
0.6346	Remote Similarity	NPD3573	Approved
0.6337	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6317	Approved
0.633	Remote Similarity	NPD4697	Phase 3
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5207	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.6306	Remote Similarity	NPD4700	Approved
0.6299	Remote Similarity	NPD7319	Approved
0.6296	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD8039	Approved
0.6286	Remote Similarity	NPD6672	Approved
0.6286	Remote Similarity	NPD5737	Approved
0.6286	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6335	Approved
0.6281	Remote Similarity	NPD6313	Approved
0.6281	Remote Similarity	NPD6314	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6262	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD4730	Approved
0.6207	Remote Similarity	NPD4729	Approved
0.6198	Remote Similarity	NPD6009	Approved
0.619	Remote Similarity	NPD7507	Approved
0.6176	Remote Similarity	NPD3667	Approved
0.616	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8074	Phase 3
0.614	Remote Similarity	NPD6647	Phase 2
0.6139	Remote Similarity	NPD4695	Discontinued
0.6129	Remote Similarity	NPD7331	Phase 2
0.6129	Remote Similarity	NPD5983	Phase 2
0.6121	Remote Similarity	NPD6412	Phase 2
0.6102	Remote Similarity	NPD5247	Approved
0.6102	Remote Similarity	NPD5248	Approved
0.6102	Remote Similarity	NPD5249	Phase 3
0.6102	Remote Similarity	NPD5250	Approved
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5251	Approved
0.609	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7260	Phase 2
0.6068	Remote Similarity	NPD5128	Approved
0.6058	Remote Similarity	NPD4786	Approved
0.6055	Remote Similarity	NPD4202	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