NPASS Compound

Structure

NPC261990 OpenBabel07101718192D 32 34 0 0 1 0 0 0 0 0999 V2000 -1.1340 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1340 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9641 -0.8660 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 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 8 24 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 25 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 2 1 1 0 0 0 16 19 1 0 0 0 0 16 31 1 0 0 0 0 17 23 1 0 0 0 0 17 25 1 1 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 31 1 0 0 0 0 22 32 1 1 0 0 0 24 5 1 6 0 0 0 24 32 1 0 0 0 0 25 6 1 1 0 0 0 26 7 1 1 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.33
Volume:	482.688
LogP:	3.819
LogD:	3.42
LogS:	-4.44
# Rotatable Bonds:	6
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	4.993
Fsp3:	0.923
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:	-4.726
MDCK Permeability:	1.9693761714734137e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	93.05780792236328%
Volume Distribution (VD):	1.547
Pgp-substrate:	6.049349784851074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.862
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.244
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.297
CYP3A4-inhibitor:	0.29
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	1.549
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.711
Carcinogencity:	0.027
Eye Corrosion:	0.024
Eye Irritation:	0.148
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC261990

Natural Product ID:	NPC261990
*Common Name:**	(13R)-Labda-14(15)-En-8,13-Diol 13-O-Beta-D-Fucopyranoside
IUPAC Name:	(2S,3R,4S,5R,6R)-2-[(3R)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QIFUWGZVLWAGTD-BICFHPTJSA-N
Standard InCHI:	InChI=1S/C26H46O6/c1-8-24(5,32-22-21(29)20(28)19(27)16(2)31-22)14-10-18-25(6)13-9-12-23(3,4)17(25)11-15-26(18,7)30/h8,16-22,27-30H,1,9-15H2,2-7H3/t16-,17+,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
SMILES:	C=C[C@](O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)O)O)(CC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCCC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457828
PubChem CID:	11619408
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO3386	Aster spathulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252909]
NPO3386	Aster spathulifolius	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17121178]
NPO3386	Aster spathulifolius	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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570930]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570930]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570930]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570930]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570930]

☑ 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 NPC261990 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	269
0.1-0.2	2241
0.2-0.3	5944
0.3-0.4	13064
0.4-0.5	9885
0.5-0.6	5446
0.6-0.7	4400
0.7-0.8	1363
0.8-0.85	70
0.85-0.9	12
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474249
0.9651	High Similarity	NPC289361
0.8889	High Similarity	NPC474835
0.8889	High Similarity	NPC91654
0.8889	High Similarity	NPC67398
0.8889	High Similarity	NPC474792
0.8804	High Similarity	NPC90583
0.8791	High Similarity	NPC305160
0.8571	High Similarity	NPC177343
0.8571	High Similarity	NPC48463
0.8511	High Similarity	NPC125551
0.8511	High Similarity	NPC96597
0.8511	High Similarity	NPC240372
0.8511	High Similarity	NPC309503
0.8511	High Similarity	NPC91197
0.8511	High Similarity	NPC239547
0.8511	High Similarity	NPC155319
0.8485	Intermediate Similarity	NPC80210
0.8485	Intermediate Similarity	NPC38376
0.8454	Intermediate Similarity	NPC473124
0.8454	Intermediate Similarity	NPC473123
0.8452	Intermediate Similarity	NPC169994
0.8438	Intermediate Similarity	NPC280991
0.8421	Intermediate Similarity	NPC312325
0.8404	Intermediate Similarity	NPC472989
0.84	Intermediate Similarity	NPC285253
0.84	Intermediate Similarity	NPC28844
0.84	Intermediate Similarity	NPC473328
0.84	Intermediate Similarity	NPC221110
0.84	Intermediate Similarity	NPC473318
0.84	Intermediate Similarity	NPC195116
0.84	Intermediate Similarity	NPC180459
0.8387	Intermediate Similarity	NPC477927
0.8387	Intermediate Similarity	NPC72817
0.8387	Intermediate Similarity	NPC211238
0.8384	Intermediate Similarity	NPC33053
0.837	Intermediate Similarity	NPC302584
0.8367	Intermediate Similarity	NPC110656
0.8367	Intermediate Similarity	NPC203354
0.8367	Intermediate Similarity	NPC473127
0.8353	Intermediate Similarity	NPC137587
0.8351	Intermediate Similarity	NPC470571
0.8333	Intermediate Similarity	NPC317019
0.8317	Intermediate Similarity	NPC65155
0.8317	Intermediate Similarity	NPC103627
0.8317	Intermediate Similarity	NPC191439
0.8317	Intermediate Similarity	NPC170974
0.8316	Intermediate Similarity	NPC473555
0.8316	Intermediate Similarity	NPC471770
0.8316	Intermediate Similarity	NPC278939
0.8295	Intermediate Similarity	NPC241959
0.8247	Intermediate Similarity	NPC472023
0.8247	Intermediate Similarity	NPC88000
0.8247	Intermediate Similarity	NPC21568
0.8247	Intermediate Similarity	NPC47566
0.8247	Intermediate Similarity	NPC285231
0.8247	Intermediate Similarity	NPC160734
0.8247	Intermediate Similarity	NPC129372
0.8247	Intermediate Similarity	NPC4831
0.8247	Intermediate Similarity	NPC309425
0.8235	Intermediate Similarity	NPC110494
0.8235	Intermediate Similarity	NPC157474
0.8235	Intermediate Similarity	NPC65034
0.8235	Intermediate Similarity	NPC208189
0.8229	Intermediate Similarity	NPC157739
0.8229	Intermediate Similarity	NPC216260
0.8229	Intermediate Similarity	NPC5358
0.8229	Intermediate Similarity	NPC234287
0.8229	Intermediate Similarity	NPC280825
0.8218	Intermediate Similarity	NPC472901
0.8202	Intermediate Similarity	NPC166279
0.82	Intermediate Similarity	NPC281939
0.8191	Intermediate Similarity	NPC96736
0.8191	Intermediate Similarity	NPC178949
0.8182	Intermediate Similarity	NPC93352
0.8163	Intermediate Similarity	NPC300399
0.8163	Intermediate Similarity	NPC471482
0.8163	Intermediate Similarity	NPC37207
0.8163	Intermediate Similarity	NPC136816
0.8155	Intermediate Similarity	NPC475354
0.8155	Intermediate Similarity	NPC476305
0.8155	Intermediate Similarity	NPC216595
0.8155	Intermediate Similarity	NPC231797
0.8155	Intermediate Similarity	NPC473567
0.8155	Intermediate Similarity	NPC473125
0.8152	Intermediate Similarity	NPC309310
0.8152	Intermediate Similarity	NPC473058
0.8144	Intermediate Similarity	NPC91497
0.8144	Intermediate Similarity	NPC473200
0.8144	Intermediate Similarity	NPC471247
0.8144	Intermediate Similarity	NPC64348
0.8144	Intermediate Similarity	NPC7341
0.814	Intermediate Similarity	NPC272841
0.8125	Intermediate Similarity	NPC76486
0.8125	Intermediate Similarity	NPC26307
0.8119	Intermediate Similarity	NPC472896
0.8119	Intermediate Similarity	NPC235824
0.8119	Intermediate Similarity	NPC472897
0.8111	Intermediate Similarity	NPC290612
0.81	Intermediate Similarity	NPC470767
0.81	Intermediate Similarity	NPC472900
0.81	Intermediate Similarity	NPC472898
0.81	Intermediate Similarity	NPC470763
0.81	Intermediate Similarity	NPC472899
0.8095	Intermediate Similarity	NPC308489
0.809	Intermediate Similarity	NPC477978
0.8081	Intermediate Similarity	NPC99627
0.8081	Intermediate Similarity	NPC471888
0.8081	Intermediate Similarity	NPC120123
0.8081	Intermediate Similarity	NPC211879
0.8081	Intermediate Similarity	NPC245280
0.8081	Intermediate Similarity	NPC473020
0.8081	Intermediate Similarity	NPC8039
0.8081	Intermediate Similarity	NPC213190
0.8081	Intermediate Similarity	NPC157659
0.8081	Intermediate Similarity	NPC31907
0.8081	Intermediate Similarity	NPC472252
0.8081	Intermediate Similarity	NPC16520
0.8081	Intermediate Similarity	NPC473198
0.8081	Intermediate Similarity	NPC286969
0.8081	Intermediate Similarity	NPC131479
0.8081	Intermediate Similarity	NPC471887
0.8081	Intermediate Similarity	NPC162354
0.8081	Intermediate Similarity	NPC114874
0.8081	Intermediate Similarity	NPC473129
0.8081	Intermediate Similarity	NPC471885
0.8081	Intermediate Similarity	NPC471886
0.8081	Intermediate Similarity	NPC189852
0.8081	Intermediate Similarity	NPC155010
0.8077	Intermediate Similarity	NPC40133
0.8077	Intermediate Similarity	NPC290608
0.8077	Intermediate Similarity	NPC44298
0.8077	Intermediate Similarity	NPC473128
0.8077	Intermediate Similarity	NPC49413
0.8065	Intermediate Similarity	NPC159876
0.8061	Intermediate Similarity	NPC263756
0.8061	Intermediate Similarity	NPC470168
0.8061	Intermediate Similarity	NPC117714
0.8058	Intermediate Similarity	NPC472987
0.8058	Intermediate Similarity	NPC473021
0.8041	Intermediate Similarity	NPC477928
0.8041	Intermediate Similarity	NPC158088
0.8039	Intermediate Similarity	NPC250089
0.8039	Intermediate Similarity	NPC14630
0.8039	Intermediate Similarity	NPC157530
0.8022	Intermediate Similarity	NPC471411
0.8022	Intermediate Similarity	NPC471410
0.8021	Intermediate Similarity	NPC207617
0.802	Intermediate Similarity	NPC231340
0.8	Intermediate Similarity	NPC273879
0.8	Intermediate Similarity	NPC187400
0.8	Intermediate Similarity	NPC54521
0.8	Intermediate Similarity	NPC312774
0.8	Intermediate Similarity	NPC57065
0.8	Intermediate Similarity	NPC476361
0.8	Intermediate Similarity	NPC165033
0.8	Intermediate Similarity	NPC221562
0.8	Intermediate Similarity	NPC109792
0.8	Intermediate Similarity	NPC75608
0.8	Intermediate Similarity	NPC470885
0.8	Intermediate Similarity	NPC475365
0.8	Intermediate Similarity	NPC476360
0.798	Intermediate Similarity	NPC52585
0.798	Intermediate Similarity	NPC228049
0.798	Intermediate Similarity	NPC288694
0.798	Intermediate Similarity	NPC159036
0.798	Intermediate Similarity	NPC150463
0.798	Intermediate Similarity	NPC76497
0.798	Intermediate Similarity	NPC213674
0.798	Intermediate Similarity	NPC312553
0.798	Intermediate Similarity	NPC30289
0.798	Intermediate Similarity	NPC214277
0.798	Intermediate Similarity	NPC68630
0.798	Intermediate Similarity	NPC256133
0.7961	Intermediate Similarity	NPC472717
0.7959	Intermediate Similarity	NPC324598
0.7957	Intermediate Similarity	NPC59682
0.7941	Intermediate Similarity	NPC476513
0.7938	Intermediate Similarity	NPC243728
0.7938	Intermediate Similarity	NPC473890
0.7935	Intermediate Similarity	NPC43912
0.7935	Intermediate Similarity	NPC140446
0.7921	Intermediate Similarity	NPC208594
0.7921	Intermediate Similarity	NPC473199
0.7921	Intermediate Similarity	NPC127801
0.7921	Intermediate Similarity	NPC152584
0.7921	Intermediate Similarity	NPC269627
0.7921	Intermediate Similarity	NPC69737
0.7921	Intermediate Similarity	NPC160816
0.7921	Intermediate Similarity	NPC194842
0.7921	Intermediate Similarity	NPC208477
0.7917	Intermediate Similarity	NPC100892
0.7917	Intermediate Similarity	NPC135224
0.7917	Intermediate Similarity	NPC477970
0.7917	Intermediate Similarity	NPC477969
0.7912	Intermediate Similarity	NPC34581
0.79	Intermediate Similarity	NPC471450
0.79	Intermediate Similarity	NPC123796
0.79	Intermediate Similarity	NPC16573
0.7895	Intermediate Similarity	NPC296620

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 NPC261990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	2577
0.2-0.3	3787
0.3-0.4	1714
0.4-0.5	472
0.5-0.6	297
0.6-0.7	57
0.7-0.8	19
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
0.7615	Intermediate Similarity	NPD7328	Approved
0.7615	Intermediate Similarity	NPD7327	Approved
0.7596	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD8133	Approved
0.7545	Intermediate Similarity	NPD7516	Approved
0.7477	Intermediate Similarity	NPD8377	Approved
0.7477	Intermediate Similarity	NPD8294	Approved
0.7429	Intermediate Similarity	NPD6686	Approved
0.7411	Intermediate Similarity	NPD8380	Approved
0.7411	Intermediate Similarity	NPD8335	Approved
0.7411	Intermediate Similarity	NPD8379	Approved
0.7411	Intermediate Similarity	NPD8378	Approved
0.7411	Intermediate Similarity	NPD7503	Approved
0.7411	Intermediate Similarity	NPD8033	Approved
0.7411	Intermediate Similarity	NPD8296	Approved
0.7273	Intermediate Similarity	NPD1810	Approved
0.7273	Intermediate Similarity	NPD1811	Approved
0.7196	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8171	Discontinued
0.717	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD7507	Approved
0.6975	Remote Similarity	NPD7319	Approved
0.6932	Remote Similarity	NPD2686	Approved
0.6932	Remote Similarity	NPD2687	Approved
0.6932	Remote Similarity	NPD2254	Approved
0.6827	Remote Similarity	NPD7638	Approved
0.681	Remote Similarity	NPD6921	Approved
0.6809	Remote Similarity	NPD7525	Registered
0.6809	Remote Similarity	NPD6928	Phase 2
0.6762	Remote Similarity	NPD7640	Approved
0.6762	Remote Similarity	NPD7639	Approved
0.6754	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6370	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7645	Phase 2
0.6698	Remote Similarity	NPD5344	Discontinued
0.6695	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD7524	Approved
0.6629	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD371	Approved
0.6598	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3669	Approved
0.6581	Remote Similarity	NPD6054	Approved
0.6556	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6514	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4225	Approved
0.6475	Remote Similarity	NPD7736	Approved
0.6441	Remote Similarity	NPD6059	Approved
0.6429	Remote Similarity	NPD6695	Phase 3
0.6393	Remote Similarity	NPD8293	Discontinued
0.6387	Remote Similarity	NPD6016	Approved
0.6387	Remote Similarity	NPD6015	Approved
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7492	Approved
0.6333	Remote Similarity	NPD5988	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.6325	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD3168	Discontinued
0.6311	Remote Similarity	NPD6616	Approved
0.6296	Remote Similarity	NPD6648	Approved
0.6281	Remote Similarity	NPD6067	Discontinued
0.6261	Remote Similarity	NPD6882	Approved
0.626	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD4159	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.6204	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7750	Discontinued
0.6174	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6319	Approved
0.6122	Remote Similarity	NPD6930	Phase 2
0.6122	Remote Similarity	NPD6931	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7339	Approved
0.6105	Remote Similarity	NPD6942	Approved
0.6095	Remote Similarity	NPD8034	Phase 2
0.6095	Remote Similarity	NPD8035	Phase 2
0.6066	Remote Similarity	NPD5125	Phase 3
0.6066	Remote Similarity	NPD5126	Approved
0.6061	Remote Similarity	NPD1780	Approved
0.6061	Remote Similarity	NPD1779	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.6042	Remote Similarity	NPD6933	Approved
0.6042	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7625	Phase 1
0.602	Remote Similarity	NPD6929	Approved
0.6019	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD8449	Approved
0.6	Remote Similarity	NPD7838	Discovery
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD46	Approved
0.5981	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6932	Approved
0.5969	Remote Similarity	NPD8450	Suspended
0.5966	Remote Similarity	NPD6940	Discontinued
0.5965	Remote Similarity	NPD5697	Approved
0.5963	Remote Similarity	NPD7902	Approved
0.596	Remote Similarity	NPD7332	Phase 2
0.596	Remote Similarity	NPD7514	Phase 3
0.5952	Remote Similarity	NPD6033	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD4634	Approved
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5943	Remote Similarity	NPD7515	Phase 2
0.5943	Remote Similarity	NPD7087	Discontinued
0.5926	Remote Similarity	NPD7991	Discontinued
0.5918	Remote Similarity	NPD7145	Approved
0.5918	Remote Similarity	NPD6697	Approved
0.5918	Remote Similarity	NPD6118	Approved
0.5918	Remote Similarity	NPD6114	Approved
0.5918	Remote Similarity	NPD6115	Approved
0.5913	Remote Similarity	NPD7320	Approved
0.5909	Remote Similarity	NPD1145	Discontinued
0.5905	Remote Similarity	NPD6051	Approved
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6649	Approved
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5897	Remote Similarity	NPD6650	Approved
0.5893	Remote Similarity	NPD5211	Phase 2
0.5888	Remote Similarity	NPD6399	Phase 3
0.5887	Remote Similarity	NPD7604	Phase 2
0.5882	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5357	Phase 1
0.5862	Remote Similarity	NPD6373	Approved
0.5862	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD6012	Approved
0.5862	Remote Similarity	NPD6372	Approved
0.5862	Remote Similarity	NPD6013	Approved
0.5856	Remote Similarity	NPD5285	Approved
0.5856	Remote Similarity	NPD4696	Approved
0.5856	Remote Similarity	NPD5286	Approved
0.5854	Remote Similarity	NPD5983	Phase 2
0.5833	Remote Similarity	NPD6924	Approved
0.5833	Remote Similarity	NPD6926	Approved
0.5826	Remote Similarity	NPD5701	Approved
0.5825	Remote Similarity	NPD6893	Approved
0.5818	Remote Similarity	NPD4755	Approved
0.5816	Remote Similarity	NPD6925	Approved
0.5816	Remote Similarity	NPD5776	Phase 2
0.5816	Remote Similarity	NPD6116	Phase 1
0.58	Remote Similarity	NPD7509	Discontinued
0.5794	Remote Similarity	NPD6411	Approved
0.5794	Remote Similarity	NPD6336	Discontinued
0.5794	Remote Similarity	NPD6079	Approved
0.5794	Remote Similarity	NPD7637	Suspended
0.5789	Remote Similarity	NPD5141	Approved
0.5776	Remote Similarity	NPD6011	Approved
0.5773	Remote Similarity	NPD8264	Approved
0.5769	Remote Similarity	NPD3618	Phase 1
0.5755	Remote Similarity	NPD5328	Approved
0.5752	Remote Similarity	NPD5226	Approved
0.5752	Remote Similarity	NPD4633	Approved
0.5752	Remote Similarity	NPD5224	Approved
0.5752	Remote Similarity	NPD5225	Approved
0.5743	Remote Similarity	NPD6898	Phase 1
0.5743	Remote Similarity	NPD6902	Approved
0.5741	Remote Similarity	NPD4202	Approved
0.5739	Remote Similarity	NPD6640	Phase 3
0.5728	Remote Similarity	NPD4786	Approved
0.5725	Remote Similarity	NPD6674	Discontinued
0.5714	Remote Similarity	NPD6117	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.5702	Remote Similarity	NPD5174	Approved
0.5702	Remote Similarity	NPD5175	Approved
0.5701	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6683	Phase 2
0.5688	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7900	Approved
0.5686	Remote Similarity	NPD3667	Approved
0.5684	Remote Similarity	NPD4787	Phase 1
0.5676	Remote Similarity	NPD6084	Phase 2
0.5676	Remote Similarity	NPD6083	Phase 2
0.567	Remote Similarity	NPD4784	Approved
0.567	Remote Similarity	NPD4785	Approved
0.5669	Remote Similarity	NPD8451	Approved
0.5664	Remote Similarity	NPD5223	Approved
0.5644	Remote Similarity	NPD4748	Discontinued
0.5641	Remote Similarity	NPD8174	Phase 2
0.563	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7150	Approved
0.5625	Remote Similarity	NPD8448	Approved
0.5625	Remote Similarity	NPD7151	Approved
0.5625	Remote Similarity	NPD7152	Approved
0.5625	Remote Similarity	NPD4243	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