NPASS Compound

Structure

NPC475302 OpenBabel07101718322D 21 22 0 0 1 0 0 0 0 0999 V2000 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4006 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 2 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 3.6685 -2.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7230 -3.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5346 -2.6180 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 8 1 0 0 0 0 3 10 2 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 9 2 1 1 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 6 0 0 0 12 7 1 1 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 10 1 1 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 18 1 6 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.15
Volume:	301.585
LogP:	2.508
LogD:	2.732
LogS:	-3.535
# Rotatable Bonds:	1
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.806
Synthetic Accessibility Score:	4.668
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.633
MDCK Permeability:	1.534089278720785e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	98.33683013916016%
Volume Distribution (VD):	0.688
Pgp-substrate:	1.5543022155761719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.281
CYP1A2-substrate:	0.795
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.257
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	11.344
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.839
Maximum Recommended Daily Dose:	0.377
Skin Sensitization:	0.364
Carcinogencity:	0.829
Eye Corrosion:	0.005
Eye Irritation:	0.023
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC475302

Natural Product ID:	NPC475302
*Common Name:**	(3Ar,4R,6R,7S,11As,E)-4-Hydroxy-7-Methoxy-6,10-Dimethyl-3-Methylene-3A,4,6,7,8,9-Hexahydrocyclodeca[B]Furan-2,5(3H,11Ah)-Dione
IUPAC Name:	(3aR,4R,6R,7S,10E,11aS)-4-hydroxy-7-methoxy-6,10-dimethyl-3-methylidene-4,6,7,8,9,11a-hexahydro-3aH-cyclodeca[b]furan-2,5-dione
Synonyms:
Standard InCHIKey:	BMWGTJJGVAZYQP-WCQDRJGZSA-N
Standard InCHI:	InChI=1S/C16H22O5/c1-8-5-6-11(20-4)9(2)14(17)15(18)13-10(3)16(19)21-12(13)7-8/h7,9,11-13,15,18H,3,5-6H2,1-2,4H3/b8-7+/t9-,11+,12+,13+,15-/m1/s1
SMILES:	CO[C@H]1CC/C(=C/[C@H]2[C@@H]([C@H](C(=O)[C@@H]1C)O)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503200
PubChem CID:	44566698
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:0001771] Germacranolides and derivatives

*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
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104492]
NPO12991	Montanoa hibiscifolia	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
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	20.0	uM	PMID[478077]
NPT2	Others	Unspecified		Activity	=	10.0	uM	PMID[478077]

☑ 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 NPC475302 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	203
0.1-0.2	1248
0.2-0.3	5070
0.3-0.4	10043
0.4-0.5	14256
0.5-0.6	6928
0.6-0.7	3885
0.7-0.8	864
0.8-0.85	141
0.85-0.9	57
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC255307
0.8864	High Similarity	NPC475461
0.8864	High Similarity	NPC305475
0.8851	High Similarity	NPC141193
0.8851	High Similarity	NPC158756
0.8851	High Similarity	NPC114979
0.8851	High Similarity	NPC96259
0.8851	High Similarity	NPC191476
0.875	High Similarity	NPC470755
0.8736	High Similarity	NPC473390
0.8736	High Similarity	NPC131669
0.8696	High Similarity	NPC469645
0.8696	High Similarity	NPC469692
0.8667	High Similarity	NPC476805
0.8667	High Similarity	NPC476803
0.8652	High Similarity	NPC261721
0.8652	High Similarity	NPC150755
0.8652	High Similarity	NPC469910
0.8636	High Similarity	NPC476804
0.8621	High Similarity	NPC229825
0.8602	High Similarity	NPC121825
0.8557	High Similarity	NPC149371
0.8539	High Similarity	NPC165162
0.8523	High Similarity	NPC474703
0.8523	High Similarity	NPC40746
0.8523	High Similarity	NPC169575
0.8506	High Similarity	NPC24417
0.8495	Intermediate Similarity	NPC165383
0.8488	Intermediate Similarity	NPC167881
0.8488	Intermediate Similarity	NPC98557
0.8478	Intermediate Similarity	NPC469368
0.8462	Intermediate Similarity	NPC475819
0.8454	Intermediate Similarity	NPC133907
0.8454	Intermediate Similarity	NPC47880
0.8454	Intermediate Similarity	NPC185141
0.8454	Intermediate Similarity	NPC164598
0.8454	Intermediate Similarity	NPC110443
0.8454	Intermediate Similarity	NPC474339
0.8454	Intermediate Similarity	NPC46998
0.8454	Intermediate Similarity	NPC128733
0.8444	Intermediate Similarity	NPC279859
0.8444	Intermediate Similarity	NPC38576
0.8438	Intermediate Similarity	NPC471144
0.8421	Intermediate Similarity	NPC230800
0.8421	Intermediate Similarity	NPC473859
0.8404	Intermediate Similarity	NPC469632
0.8384	Intermediate Similarity	NPC472756
0.8367	Intermediate Similarity	NPC471148
0.8351	Intermediate Similarity	NPC288876
0.8333	Intermediate Similarity	NPC261380
0.8316	Intermediate Similarity	NPC471142
0.8316	Intermediate Similarity	NPC475659
0.8315	Intermediate Similarity	NPC59097
0.8298	Intermediate Similarity	NPC273579
0.8298	Intermediate Similarity	NPC125674
0.8298	Intermediate Similarity	NPC288240
0.8298	Intermediate Similarity	NPC475838
0.8298	Intermediate Similarity	NPC295204
0.8298	Intermediate Similarity	NPC162205
0.8298	Intermediate Similarity	NPC228451
0.8295	Intermediate Similarity	NPC281949
0.8295	Intermediate Similarity	NPC52861
0.8295	Intermediate Similarity	NPC301477
0.8295	Intermediate Similarity	NPC25684
0.8283	Intermediate Similarity	NPC475945
0.8283	Intermediate Similarity	NPC475871
0.828	Intermediate Similarity	NPC144133
0.828	Intermediate Similarity	NPC179394
0.828	Intermediate Similarity	NPC475855
0.828	Intermediate Similarity	NPC129419
0.828	Intermediate Similarity	NPC474232
0.8276	Intermediate Similarity	NPC270126
0.8265	Intermediate Similarity	NPC201718
0.8265	Intermediate Similarity	NPC476270
0.8256	Intermediate Similarity	NPC141789
0.8256	Intermediate Similarity	NPC171204
0.8256	Intermediate Similarity	NPC476028
0.8247	Intermediate Similarity	NPC54843
0.8247	Intermediate Similarity	NPC141191
0.8218	Intermediate Similarity	NPC477513
0.8211	Intermediate Similarity	NPC474247
0.8202	Intermediate Similarity	NPC173609
0.8202	Intermediate Similarity	NPC89555
0.8191	Intermediate Similarity	NPC261607
0.8191	Intermediate Similarity	NPC20713
0.8191	Intermediate Similarity	NPC111114
0.8191	Intermediate Similarity	NPC300312
0.8182	Intermediate Similarity	NPC474747
0.8182	Intermediate Similarity	NPC320019
0.8182	Intermediate Similarity	NPC324017
0.8172	Intermediate Similarity	NPC268298
0.8172	Intermediate Similarity	NPC474032
0.8163	Intermediate Similarity	NPC475949
0.8161	Intermediate Similarity	NPC196653
0.8161	Intermediate Similarity	NPC471465
0.8152	Intermediate Similarity	NPC266957
0.8144	Intermediate Similarity	NPC169205
0.814	Intermediate Similarity	NPC235906
0.8125	Intermediate Similarity	NPC477922
0.8125	Intermediate Similarity	NPC275960
0.8125	Intermediate Similarity	NPC48803
0.8125	Intermediate Similarity	NPC90121
0.8125	Intermediate Similarity	NPC474947
0.8125	Intermediate Similarity	NPC193645
0.8105	Intermediate Similarity	NPC475912
0.81	Intermediate Similarity	NPC472755
0.81	Intermediate Similarity	NPC475873
0.809	Intermediate Similarity	NPC141810
0.8085	Intermediate Similarity	NPC329857
0.8085	Intermediate Similarity	NPC469718
0.8085	Intermediate Similarity	NPC473619
0.8081	Intermediate Similarity	NPC472753
0.8081	Intermediate Similarity	NPC474742
0.8081	Intermediate Similarity	NPC15993
0.8068	Intermediate Similarity	NPC19841
0.8068	Intermediate Similarity	NPC89128
0.8068	Intermediate Similarity	NPC470239
0.8068	Intermediate Similarity	NPC470244
0.8065	Intermediate Similarity	NPC475902
0.8065	Intermediate Similarity	NPC202672
0.8065	Intermediate Similarity	NPC471047
0.8065	Intermediate Similarity	NPC469628
0.8065	Intermediate Similarity	NPC475906
0.8065	Intermediate Similarity	NPC469631
0.8065	Intermediate Similarity	NPC473715
0.8065	Intermediate Similarity	NPC477302
0.8065	Intermediate Similarity	NPC469653
0.8046	Intermediate Similarity	NPC116177
0.8046	Intermediate Similarity	NPC320630
0.8046	Intermediate Similarity	NPC7563
0.8046	Intermediate Similarity	NPC474760
0.8043	Intermediate Similarity	NPC469483
0.8043	Intermediate Similarity	NPC50637
0.8041	Intermediate Similarity	NPC477921
0.8041	Intermediate Similarity	NPC279621
0.8041	Intermediate Similarity	NPC76862
0.8041	Intermediate Similarity	NPC158416
0.8041	Intermediate Similarity	NPC185553
0.8041	Intermediate Similarity	NPC476275
0.8041	Intermediate Similarity	NPC39859
0.8041	Intermediate Similarity	NPC470883
0.8023	Intermediate Similarity	NPC155587
0.8021	Intermediate Similarity	NPC140543
0.8021	Intermediate Similarity	NPC57405
0.8021	Intermediate Similarity	NPC303942
0.802	Intermediate Similarity	NPC474741
0.8	Intermediate Similarity	NPC30515
0.8	Intermediate Similarity	NPC85772
0.8	Intermediate Similarity	NPC473321
0.8	Intermediate Similarity	NPC184463
0.8	Intermediate Similarity	NPC472754
0.7979	Intermediate Similarity	NPC166919
0.7979	Intermediate Similarity	NPC218927
0.7979	Intermediate Similarity	NPC206001
0.7979	Intermediate Similarity	NPC295312
0.7978	Intermediate Similarity	NPC281132
0.7959	Intermediate Similarity	NPC323421
0.7959	Intermediate Similarity	NPC471140
0.7959	Intermediate Similarity	NPC328562
0.7955	Intermediate Similarity	NPC108816
0.7955	Intermediate Similarity	NPC93763
0.7938	Intermediate Similarity	NPC36954
0.7938	Intermediate Similarity	NPC471141
0.7938	Intermediate Similarity	NPC270013
0.7938	Intermediate Similarity	NPC14961
0.7931	Intermediate Similarity	NPC68819
0.7921	Intermediate Similarity	NPC4620
0.7917	Intermediate Similarity	NPC212486
0.7917	Intermediate Similarity	NPC476300
0.7917	Intermediate Similarity	NPC81419
0.7917	Intermediate Similarity	NPC179746
0.7912	Intermediate Similarity	NPC318468
0.7912	Intermediate Similarity	NPC116543
0.79	Intermediate Similarity	NPC264477
0.79	Intermediate Similarity	NPC477511
0.7895	Intermediate Similarity	NPC51004
0.7895	Intermediate Similarity	NPC71533
0.7895	Intermediate Similarity	NPC316228
0.7895	Intermediate Similarity	NPC106510
0.7889	Intermediate Similarity	NPC470241
0.7885	Intermediate Similarity	NPC38154
0.7879	Intermediate Similarity	NPC473326
0.7872	Intermediate Similarity	NPC287089
0.7872	Intermediate Similarity	NPC136879
0.7865	Intermediate Similarity	NPC617
0.7857	Intermediate Similarity	NPC17585
0.7857	Intermediate Similarity	NPC31645
0.7857	Intermediate Similarity	NPC476315
0.7857	Intermediate Similarity	NPC184065
0.7857	Intermediate Similarity	NPC476009
0.7849	Intermediate Similarity	NPC107787
0.7843	Intermediate Similarity	NPC220964
0.7843	Intermediate Similarity	NPC203659
0.7843	Intermediate Similarity	NPC100487
0.7843	Intermediate Similarity	NPC475676
0.7841	Intermediate Similarity	NPC470240
0.7841	Intermediate Similarity	NPC476794
0.7841	Intermediate Similarity	NPC65603
0.7841	Intermediate Similarity	NPC97516
0.7835	Intermediate Similarity	NPC476267

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 NPC475302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1841
0.2-0.3	3712
0.3-0.4	2226
0.4-0.5	765
0.5-0.6	301
0.6-0.7	96
0.7-0.8	16
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
0.8125	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5785	Approved
0.7524	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5363	Approved
0.7368	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5786	Approved
0.7234	Intermediate Similarity	NPD4269	Approved
0.7234	Intermediate Similarity	NPD4270	Approved
0.7184	Intermediate Similarity	NPD4225	Approved
0.7172	Intermediate Similarity	NPD6698	Approved
0.7172	Intermediate Similarity	NPD46	Approved
0.7158	Intermediate Similarity	NPD7154	Phase 3
0.7156	Intermediate Similarity	NPD6371	Approved
0.7129	Intermediate Similarity	NPD5282	Discontinued
0.7128	Intermediate Similarity	NPD5369	Approved
0.71	Intermediate Similarity	NPD7983	Approved
0.7053	Intermediate Similarity	NPD6435	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.703	Intermediate Similarity	NPD5778	Approved
0.7021	Intermediate Similarity	NPD4252	Approved
0.69	Remote Similarity	NPD1695	Approved
0.69	Remote Similarity	NPD6101	Approved
0.69	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5368	Approved
0.6842	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1694	Approved
0.6837	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7838	Discovery
0.6804	Remote Similarity	NPD5362	Discontinued
0.6786	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD5209	Approved
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6638	Remote Similarity	NPD7115	Discovery
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4268	Approved
0.6632	Remote Similarity	NPD4271	Approved
0.66	Remote Similarity	NPD4249	Approved
0.6577	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD5370	Suspended
0.6538	Remote Similarity	NPD6399	Phase 3
0.6535	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD4251	Approved
0.6526	Remote Similarity	NPD4756	Discovery
0.6518	Remote Similarity	NPD6899	Approved
0.6518	Remote Similarity	NPD6881	Approved
0.6518	Remote Similarity	NPD6686	Approved
0.6491	Remote Similarity	NPD6650	Approved
0.6491	Remote Similarity	NPD6649	Approved
0.6486	Remote Similarity	NPD6402	Approved
0.6486	Remote Similarity	NPD7128	Approved
0.6486	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD6675	Approved
0.646	Remote Similarity	NPD6012	Approved
0.646	Remote Similarity	NPD6372	Approved
0.646	Remote Similarity	NPD6013	Approved
0.646	Remote Similarity	NPD6014	Approved
0.646	Remote Similarity	NPD6373	Approved
0.6449	Remote Similarity	NPD6083	Phase 2
0.6449	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD5701	Approved
0.6415	Remote Similarity	NPD5695	Phase 3
0.6415	Remote Similarity	NPD5210	Approved
0.6415	Remote Similarity	NPD4629	Approved
0.6404	Remote Similarity	NPD7102	Approved
0.6404	Remote Similarity	NPD6883	Approved
0.6404	Remote Similarity	NPD7290	Approved
0.6389	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6011	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6364	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6847	Approved
0.6348	Remote Similarity	NPD6617	Approved
0.6348	Remote Similarity	NPD6869	Approved
0.6348	Remote Similarity	NPD8130	Phase 1
0.63	Remote Similarity	NPD5331	Approved
0.63	Remote Similarity	NPD5332	Approved
0.6293	Remote Similarity	NPD6882	Approved
0.6293	Remote Similarity	NPD8297	Approved
0.6286	Remote Similarity	NPD7637	Suspended
0.6281	Remote Similarity	NPD8516	Approved
0.6281	Remote Similarity	NPD8517	Approved
0.6281	Remote Similarity	NPD8513	Phase 3
0.6281	Remote Similarity	NPD8515	Approved
0.6263	Remote Similarity	NPD4790	Discontinued
0.6239	Remote Similarity	NPD7638	Approved
0.6238	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7260	Phase 2
0.6216	Remote Similarity	NPD5211	Phase 2
0.6207	Remote Similarity	NPD2204	Approved
0.6198	Remote Similarity	NPD6319	Approved
0.6182	Remote Similarity	NPD7639	Approved
0.6182	Remote Similarity	NPD5286	Approved
0.6182	Remote Similarity	NPD5285	Approved
0.6182	Remote Similarity	NPD7640	Approved
0.6182	Remote Similarity	NPD4696	Approved
0.6162	Remote Similarity	NPD4695	Discontinued
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6148	Remote Similarity	NPD8444	Approved
0.6147	Remote Similarity	NPD7902	Approved
0.6147	Remote Similarity	NPD4755	Approved
0.6146	Remote Similarity	NPD8039	Approved
0.6134	Remote Similarity	NPD6274	Approved
0.6132	Remote Similarity	NPD5693	Phase 1
0.6129	Remote Similarity	NPD7492	Approved
0.6126	Remote Similarity	NPD5344	Discontinued
0.6117	Remote Similarity	NPD5279	Phase 3
0.6111	Remote Similarity	NPD3197	Phase 1
0.6106	Remote Similarity	NPD5141	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.608	Remote Similarity	NPD6616	Approved
0.6071	Remote Similarity	NPD4633	Approved
0.6071	Remote Similarity	NPD5225	Approved
0.6071	Remote Similarity	NPD5224	Approved
0.6071	Remote Similarity	NPD5226	Approved
0.6068	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6054	Approved
0.6055	Remote Similarity	NPD4697	Phase 3
0.6055	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5222	Approved
0.6055	Remote Similarity	NPD5221	Approved
0.6048	Remote Similarity	NPD7642	Approved
0.6047	Remote Similarity	NPD6845	Suspended
0.604	Remote Similarity	NPD3667	Approved
0.6036	Remote Similarity	NPD4700	Approved
0.6032	Remote Similarity	NPD7078	Approved
0.6032	Remote Similarity	NPD8074	Phase 3
0.6019	Remote Similarity	NPD7748	Approved
0.6018	Remote Similarity	NPD5174	Approved
0.6018	Remote Similarity	NPD5175	Approved
0.6016	Remote Similarity	NPD6016	Approved
0.6016	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7736	Approved
0.5984	Remote Similarity	NPD7101	Approved
0.5984	Remote Similarity	NPD7100	Approved
0.5983	Remote Similarity	NPD4634	Approved
0.5982	Remote Similarity	NPD5223	Approved
0.5981	Remote Similarity	NPD7515	Phase 2
0.598	Remote Similarity	NPD6110	Phase 1
0.5978	Remote Similarity	NPD7331	Phase 2
0.5978	Remote Similarity	NPD3704	Approved
0.5968	Remote Similarity	NPD5988	Approved
0.5968	Remote Similarity	NPD6370	Approved
0.5966	Remote Similarity	NPD4632	Approved
0.5962	Remote Similarity	NPD6422	Discontinued
0.5962	Remote Similarity	NPD6684	Approved
0.5962	Remote Similarity	NPD7334	Approved
0.5962	Remote Similarity	NPD7521	Approved
0.5962	Remote Similarity	NPD7146	Approved
0.5962	Remote Similarity	NPD6409	Approved
0.5962	Remote Similarity	NPD5330	Approved
0.5962	Remote Similarity	NPD3618	Phase 1
0.595	Remote Similarity	NPD6317	Approved
0.5935	Remote Similarity	NPD6059	Approved
0.5922	Remote Similarity	NPD3666	Approved
0.5922	Remote Similarity	NPD3665	Phase 1
0.5922	Remote Similarity	NPD3133	Approved
0.5922	Remote Similarity	NPD4786	Approved
0.592	Remote Similarity	NPD8328	Phase 3
0.592	Remote Similarity	NPD7829	Approved
0.592	Remote Similarity	NPD7830	Approved
0.5913	Remote Similarity	NPD6008	Approved
0.5906	Remote Similarity	NPD8293	Discontinued
0.5902	Remote Similarity	NPD6314	Approved
0.5902	Remote Similarity	NPD6335	Approved
0.5902	Remote Similarity	NPD6313	Approved
0.5897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6648	Approved
0.5872	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7900	Approved
0.587	Remote Similarity	NPD7341	Phase 2
0.5868	Remote Similarity	NPD6868	Approved
0.5865	Remote Similarity	NPD1696	Phase 3
0.5849	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6903	Approved
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD2067	Discontinued
0.5842	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5284	Approved
0.5833	Remote Similarity	NPD5281	Approved
0.5833	Remote Similarity	NPD6079	Approved
0.5827	Remote Similarity	NPD8451	Approved
0.582	Remote Similarity	NPD6009	Approved
0.5814	Remote Similarity	NPD7319	Approved
0.5812	Remote Similarity	NPD4730	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