NPASS Compound

Structure

CID252809 OpenBabel06191716052D 21 22 0 0 1 0 0 0 0 0999 V2000 1.2761 1.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3762 1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9523 1.3454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4725 -3.6797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7898 -1.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3317 -1.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1424 -0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9600 -2.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4805 0.7151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5355 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1466 -2.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2805 -2.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1538 -1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6620 -0.7495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2999 0.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4523 0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1454 -2.7347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9174 -0.3980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8223 -1.3935 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6762 0.7367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 5 1 6 0 0 0 20 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.26
Volume:	340.881
LogP:	5.256
LogD:	4.874
LogS:	-5.935
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.641
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.602
MDCK Permeability:	1.8923163224826567e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.818
30% Bioavailability (F30%):	0.816

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.498
Plasma Protein Binding (PPB):	97.5437240600586%
Volume Distribution (VD):	1.642
Pgp-substrate:	1.9664009809494019%

ADMET: Metabolism

CYP1A2-inhibitor:	0.171
CYP1A2-substrate:	0.413
CYP2C19-inhibitor:	0.31
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.552
CYP2D6-substrate:	0.628
CYP3A4-inhibitor:	0.521
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	4.693
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.95
Carcinogencity:	0.012
Eye Corrosion:	0.915
Eye Irritation:	0.915
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC252809

Natural Product ID:	NPC252809
*Common Name:**	(1R,3E,7E,11R,12R)-12-Hydroxy-3,7-Dolabelladiene
IUPAC Name:	(1R,3aR,5E,9E,12aR)-3a,6,10-trimethyl-1-propan-2-yl-2,3,4,7,8,11,12,12a-octahydrocyclopenta[11]annulen-1-ol
Synonyms:
Standard InCHIKey:	RVTWKSHZFSEJRD-RGYXUMAVSA-N
Standard InCHI:	InChI=1S/C20H34O/c1-15(2)20(21)14-13-19(5)12-11-17(4)8-6-7-16(3)9-10-18(19)20/h7,11,15,18,21H,6,8-10,12-14H2,1-5H3/b16-7+,17-11+/t18-,19+,20-/m1/s1
SMILES:	C/C/1=CC[C@@]2(C)CC[C@@]([C@@H]2CC/C(=C/CC1)/C)(O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689084
PubChem CID:	51040258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	at a depth of 0.1-1 m, Elafonissos Island (3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	Elafonissos Island (GPS coordinates 3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29313	Halomonas meridiana	Species	Halomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29146	Polygonatum kingianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29308	Mycobacterium marinum	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29285	Dendrobium densiflorum	Species	Orchidaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[490317]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[490317]

☑ 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 NPC252809 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	155
0.1-0.2	2490
0.2-0.3	16850
0.3-0.4	10579
0.4-0.5	7801
0.5-0.6	3848
0.6-0.7	855
0.7-0.8	95
0.8-0.85	11
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC474480
0.9474	High Similarity	NPC5698
0.931	High Similarity	NPC323153
0.9016	High Similarity	NPC238352
0.9016	High Similarity	NPC477009
0.8833	High Similarity	NPC210346
0.8814	High Similarity	NPC469321
0.8525	High Similarity	NPC63111
0.8485	Intermediate Similarity	NPC471660
0.8475	Intermediate Similarity	NPC278550
0.8361	Intermediate Similarity	NPC135648
0.8308	Intermediate Similarity	NPC224532
0.8254	Intermediate Similarity	NPC309300
0.8235	Intermediate Similarity	NPC471659
0.8214	Intermediate Similarity	NPC329773
0.8197	Intermediate Similarity	NPC184049
0.8197	Intermediate Similarity	NPC99480
0.8125	Intermediate Similarity	NPC469326
0.8125	Intermediate Similarity	NPC205618
0.8125	Intermediate Similarity	NPC261782
0.8116	Intermediate Similarity	NPC251435
0.806	Intermediate Similarity	NPC475728
0.8	Intermediate Similarity	NPC310643
0.7969	Intermediate Similarity	NPC287744
0.7969	Intermediate Similarity	NPC140233
0.7941	Intermediate Similarity	NPC41886
0.7937	Intermediate Similarity	NPC15152
0.791	Intermediate Similarity	NPC144647
0.7879	Intermediate Similarity	NPC136813
0.7846	Intermediate Similarity	NPC19569
0.7812	Intermediate Similarity	NPC279200
0.7761	Intermediate Similarity	NPC160209
0.7746	Intermediate Similarity	NPC471658
0.7714	Intermediate Similarity	NPC329090
0.7714	Intermediate Similarity	NPC309178
0.7714	Intermediate Similarity	NPC27395
0.7681	Intermediate Similarity	NPC471662
0.7656	Intermediate Similarity	NPC274704
0.7647	Intermediate Similarity	NPC22301
0.7647	Intermediate Similarity	NPC167272
0.7647	Intermediate Similarity	NPC269877
0.7627	Intermediate Similarity	NPC35519
0.7627	Intermediate Similarity	NPC179169
0.7627	Intermediate Similarity	NPC181255
0.7627	Intermediate Similarity	NPC306195
0.7627	Intermediate Similarity	NPC157781
0.7619	Intermediate Similarity	NPC310228
0.7619	Intermediate Similarity	NPC52431
0.7612	Intermediate Similarity	NPC477791
0.7612	Intermediate Similarity	NPC472253
0.7612	Intermediate Similarity	NPC472255
0.7606	Intermediate Similarity	NPC113639
0.7606	Intermediate Similarity	NPC319090
0.7606	Intermediate Similarity	NPC77501
0.7606	Intermediate Similarity	NPC328104
0.7571	Intermediate Similarity	NPC234527
0.7571	Intermediate Similarity	NPC14352
0.7571	Intermediate Similarity	NPC474140
0.7536	Intermediate Similarity	NPC9161
0.7536	Intermediate Similarity	NPC471781
0.7536	Intermediate Similarity	NPC49422
0.7534	Intermediate Similarity	NPC477514
0.7534	Intermediate Similarity	NPC477522
0.75	Intermediate Similarity	NPC315261
0.75	Intermediate Similarity	NPC162109
0.75	Intermediate Similarity	NPC192962
0.75	Intermediate Similarity	NPC167527
0.75	Intermediate Similarity	NPC126969
0.75	Intermediate Similarity	NPC49088
0.7467	Intermediate Similarity	NPC471661
0.7463	Intermediate Similarity	NPC162309
0.7463	Intermediate Similarity	NPC279434
0.7463	Intermediate Similarity	NPC272125
0.7458	Intermediate Similarity	NPC26906
0.7458	Intermediate Similarity	NPC214584
0.7432	Intermediate Similarity	NPC1319
0.7424	Intermediate Similarity	NPC290367
0.7424	Intermediate Similarity	NPC225415
0.7419	Intermediate Similarity	NPC274396
0.7397	Intermediate Similarity	NPC198968
0.7397	Intermediate Similarity	NPC155986
0.7397	Intermediate Similarity	NPC318495
0.7385	Intermediate Similarity	NPC475251
0.7368	Intermediate Similarity	NPC323445
0.7368	Intermediate Similarity	NPC472465
0.7361	Intermediate Similarity	NPC230301
0.7361	Intermediate Similarity	NPC304309
0.7361	Intermediate Similarity	NPC22105
0.7361	Intermediate Similarity	NPC288035
0.7361	Intermediate Similarity	NPC285893
0.7361	Intermediate Similarity	NPC471723
0.7361	Intermediate Similarity	NPC136188
0.7361	Intermediate Similarity	NPC134847
0.7361	Intermediate Similarity	NPC28657
0.7361	Intermediate Similarity	NPC162742
0.7361	Intermediate Similarity	NPC257347
0.7361	Intermediate Similarity	NPC313185
0.7361	Intermediate Similarity	NPC141071
0.7333	Intermediate Similarity	NPC471656
0.7333	Intermediate Similarity	NPC26117
0.7324	Intermediate Similarity	NPC469320
0.7324	Intermediate Similarity	NPC300940
0.7297	Intermediate Similarity	NPC285761
0.7286	Intermediate Similarity	NPC470041
0.7273	Intermediate Similarity	NPC211291
0.7273	Intermediate Similarity	NPC133368
0.726	Intermediate Similarity	NPC189883
0.726	Intermediate Similarity	NPC321381
0.726	Intermediate Similarity	NPC247325
0.726	Intermediate Similarity	NPC113733
0.726	Intermediate Similarity	NPC107059
0.726	Intermediate Similarity	NPC300324
0.726	Intermediate Similarity	NPC476317
0.726	Intermediate Similarity	NPC244488
0.726	Intermediate Similarity	NPC321016
0.726	Intermediate Similarity	NPC46160
0.726	Intermediate Similarity	NPC202642
0.726	Intermediate Similarity	NPC129165
0.726	Intermediate Similarity	NPC240604
0.726	Intermediate Similarity	NPC96319
0.726	Intermediate Similarity	NPC134330
0.726	Intermediate Similarity	NPC237460
0.726	Intermediate Similarity	NPC470362
0.7258	Intermediate Similarity	NPC218525
0.7246	Intermediate Similarity	NPC94192
0.7237	Intermediate Similarity	NPC472471
0.7231	Intermediate Similarity	NPC471081
0.72	Intermediate Similarity	NPC215843
0.72	Intermediate Similarity	NPC80530
0.72	Intermediate Similarity	NPC328714
0.72	Intermediate Similarity	NPC273410
0.7188	Intermediate Similarity	NPC10017
0.7183	Intermediate Similarity	NPC469737
0.7164	Intermediate Similarity	NPC219940
0.7162	Intermediate Similarity	NPC34019
0.7162	Intermediate Similarity	NPC214570
0.7162	Intermediate Similarity	NPC276769
0.7162	Intermediate Similarity	NPC186109
0.7143	Intermediate Similarity	NPC39068
0.7143	Intermediate Similarity	NPC1272
0.7143	Intermediate Similarity	NPC476431
0.7143	Intermediate Similarity	NPC179024
0.7143	Intermediate Similarity	NPC256750
0.7143	Intermediate Similarity	NPC193347
0.7143	Intermediate Similarity	NPC20262
0.7143	Intermediate Similarity	NPC201852
0.7143	Intermediate Similarity	NPC470614
0.7123	Intermediate Similarity	NPC118508
0.7123	Intermediate Similarity	NPC322353
0.7123	Intermediate Similarity	NPC121744
0.7123	Intermediate Similarity	NPC471468
0.7121	Intermediate Similarity	NPC41160
0.7105	Intermediate Similarity	NPC102253
0.7105	Intermediate Similarity	NPC164218
0.7105	Intermediate Similarity	NPC241290
0.7105	Intermediate Similarity	NPC13554
0.7105	Intermediate Similarity	NPC164840
0.7105	Intermediate Similarity	NPC324772
0.7105	Intermediate Similarity	NPC209944
0.7105	Intermediate Similarity	NPC322313
0.7105	Intermediate Similarity	NPC236237
0.7101	Intermediate Similarity	NPC114651
0.7089	Intermediate Similarity	NPC474349
0.7089	Intermediate Similarity	NPC474189
0.7089	Intermediate Similarity	NPC318390
0.7077	Intermediate Similarity	NPC122239
0.7077	Intermediate Similarity	NPC475931
0.7067	Intermediate Similarity	NPC302041
0.7067	Intermediate Similarity	NPC167037
0.7067	Intermediate Similarity	NPC18603
0.7067	Intermediate Similarity	NPC205455
0.7067	Intermediate Similarity	NPC138621
0.7067	Intermediate Similarity	NPC186191
0.7067	Intermediate Similarity	NPC275910
0.7067	Intermediate Similarity	NPC307965
0.7067	Intermediate Similarity	NPC87604
0.7067	Intermediate Similarity	NPC474216
0.7067	Intermediate Similarity	NPC244385
0.7067	Intermediate Similarity	NPC473943
0.7067	Intermediate Similarity	NPC65897
0.7067	Intermediate Similarity	NPC6978
0.7067	Intermediate Similarity	NPC85346
0.7067	Intermediate Similarity	NPC76931
0.7051	Intermediate Similarity	NPC110778
0.7051	Intermediate Similarity	NPC472473
0.7051	Intermediate Similarity	NPC477818
0.7049	Intermediate Similarity	NPC71506
0.7049	Intermediate Similarity	NPC177112
0.7042	Intermediate Similarity	NPC133873
0.7042	Intermediate Similarity	NPC254845
0.7031	Intermediate Similarity	NPC49575
0.7031	Intermediate Similarity	NPC267626
0.7031	Intermediate Similarity	NPC230823
0.7031	Intermediate Similarity	NPC55004
0.7027	Intermediate Similarity	NPC215481
0.7027	Intermediate Similarity	NPC73875
0.7015	Intermediate Similarity	NPC81615
0.7015	Intermediate Similarity	NPC474155
0.7015	Intermediate Similarity	NPC473759
0.7013	Intermediate Similarity	NPC264245

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 NPC252809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	3024
0.2-0.3	4221
0.3-0.4	1192
0.4-0.5	281
0.5-0.6	184
0.6-0.7	77
0.7-0.8	13
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
0.8485	Intermediate Similarity	NPD4243	Approved
0.8235	Intermediate Similarity	NPD4784	Approved
0.8235	Intermediate Similarity	NPD4785	Approved
0.7857	Intermediate Similarity	NPD4190	Phase 3
0.7857	Intermediate Similarity	NPD5275	Approved
0.7714	Intermediate Similarity	NPD6926	Approved
0.7714	Intermediate Similarity	NPD6924	Approved
0.7647	Intermediate Similarity	NPD6923	Approved
0.7647	Intermediate Similarity	NPD6922	Approved
0.7536	Intermediate Similarity	NPD7143	Approved
0.7536	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD6933	Approved
0.7432	Intermediate Similarity	NPD4195	Approved
0.7429	Intermediate Similarity	NPD7151	Approved
0.7429	Intermediate Similarity	NPD7152	Approved
0.7429	Intermediate Similarity	NPD7150	Approved
0.7361	Intermediate Similarity	NPD7339	Approved
0.7361	Intermediate Similarity	NPD6942	Approved
0.726	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6932	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7105	Intermediate Similarity	NPD6931	Approved
0.7105	Intermediate Similarity	NPD6930	Phase 2
0.7105	Intermediate Similarity	NPD7525	Registered
0.7089	Intermediate Similarity	NPD5329	Approved
0.6974	Remote Similarity	NPD6683	Phase 2
0.6974	Remote Similarity	NPD6929	Approved
0.6962	Remote Similarity	NPD4197	Approved
0.6933	Remote Similarity	NPD5776	Phase 2
0.6933	Remote Similarity	NPD6925	Approved
0.6883	Remote Similarity	NPD7514	Phase 3
0.6883	Remote Similarity	NPD7509	Discontinued
0.6842	Remote Similarity	NPD7145	Approved
0.6842	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6695	Phase 3
0.679	Remote Similarity	NPD4690	Approved
0.679	Remote Similarity	NPD4693	Phase 3
0.679	Remote Similarity	NPD5205	Approved
0.679	Remote Similarity	NPD4694	Approved
0.679	Remote Similarity	NPD4688	Approved
0.679	Remote Similarity	NPD5280	Approved
0.679	Remote Similarity	NPD4138	Approved
0.679	Remote Similarity	NPD5690	Phase 2
0.679	Remote Similarity	NPD4689	Approved
0.675	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4748	Discontinued
0.6627	Remote Similarity	NPD4518	Approved
0.6627	Remote Similarity	NPD4723	Approved
0.6627	Remote Similarity	NPD4722	Approved
0.6625	Remote Similarity	NPD5332	Approved
0.6625	Remote Similarity	NPD5362	Discontinued
0.6625	Remote Similarity	NPD5331	Approved
0.6623	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4692	Approved
0.6582	Remote Similarity	NPD6898	Phase 1
0.6582	Remote Similarity	NPD5369	Approved
0.6582	Remote Similarity	NPD4139	Approved
0.6582	Remote Similarity	NPD6902	Approved
0.6582	Remote Similarity	NPD4790	Discontinued
0.6548	Remote Similarity	NPD4753	Phase 2
0.6543	Remote Similarity	NPD4786	Approved
0.6543	Remote Similarity	NPD3133	Approved
0.6543	Remote Similarity	NPD3666	Approved
0.6543	Remote Similarity	NPD3665	Phase 1
0.6506	Remote Similarity	NPD7524	Approved
0.6506	Remote Similarity	NPD7750	Discontinued
0.6479	Remote Similarity	NPD7331	Phase 2
0.6471	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4096	Approved
0.6463	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5368	Approved
0.642	Remote Similarity	NPD4788	Approved
0.641	Remote Similarity	NPD4271	Approved
0.641	Remote Similarity	NPD4268	Approved
0.6395	Remote Similarity	NPD5284	Approved
0.6395	Remote Similarity	NPD5281	Approved
0.6386	Remote Similarity	NPD6098	Approved
0.6377	Remote Similarity	NPD368	Approved
0.6322	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD6435	Approved
0.6296	Remote Similarity	NPD3667	Approved
0.6296	Remote Similarity	NPD4269	Approved
0.6296	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD8264	Approved
0.6222	Remote Similarity	NPD6084	Phase 2
0.6222	Remote Similarity	NPD6083	Phase 2
0.6212	Remote Similarity	NPD342	Phase 1
0.6207	Remote Similarity	NPD7087	Discontinued
0.619	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5279	Phase 3
0.618	Remote Similarity	NPD4629	Approved
0.618	Remote Similarity	NPD5210	Approved
0.618	Remote Similarity	NPD5695	Phase 3
0.6163	Remote Similarity	NPD6080	Approved
0.6163	Remote Similarity	NPD5328	Approved
0.6163	Remote Similarity	NPD6051	Approved
0.6163	Remote Similarity	NPD6904	Approved
0.6163	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD1346	Approved
0.6136	Remote Similarity	NPD5133	Approved
0.6125	Remote Similarity	NPD7645	Phase 2
0.6111	Remote Similarity	NPD7341	Phase 2
0.6092	Remote Similarity	NPD5785	Approved
0.6071	Remote Similarity	NPD5363	Approved
0.6049	Remote Similarity	NPD4252	Approved
0.6047	Remote Similarity	NPD5208	Approved
0.6044	Remote Similarity	NPD4755	Approved
0.6023	Remote Similarity	NPD6050	Approved
0.6023	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD3617	Approved
0.5978	Remote Similarity	NPD5696	Approved
0.5955	Remote Similarity	NPD6399	Phase 3
0.5952	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4747	Approved
0.5914	Remote Similarity	NPD4696	Approved
0.5914	Remote Similarity	NPD5286	Approved
0.5914	Remote Similarity	NPD5285	Approved
0.5914	Remote Similarity	NPD4700	Approved
0.5909	Remote Similarity	NPD5207	Approved
0.5909	Remote Similarity	NPD5692	Phase 3
0.5897	Remote Similarity	NPD5733	Approved
0.5889	Remote Similarity	NPD5707	Approved
0.5882	Remote Similarity	NPD4219	Approved
0.5867	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6903	Approved
0.5854	Remote Similarity	NPD4695	Discontinued
0.5851	Remote Similarity	NPD5223	Approved
0.5844	Remote Similarity	NPD5276	Approved
0.5843	Remote Similarity	NPD7637	Suspended
0.5843	Remote Similarity	NPD5693	Phase 1
0.5843	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD7154	Phase 3
0.5824	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4519	Discontinued
0.5814	Remote Similarity	NPD4623	Approved
0.5789	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD5224	Approved
0.5789	Remote Similarity	NPD5091	Approved
0.5789	Remote Similarity	NPD1082	Approved
0.5789	Remote Similarity	NPD5225	Approved
0.5789	Remote Similarity	NPD5226	Approved
0.5789	Remote Similarity	NPD4137	Phase 3
0.5789	Remote Similarity	NPD791	Approved
0.5789	Remote Similarity	NPD15	Approved
0.5789	Remote Similarity	NPD5211	Phase 2
0.5783	Remote Similarity	NPD857	Phase 3
0.5773	Remote Similarity	NPD7128	Approved
0.5773	Remote Similarity	NPD6402	Approved
0.5773	Remote Similarity	NPD5739	Approved
0.5773	Remote Similarity	NPD6675	Approved
0.5765	Remote Similarity	NPD3668	Phase 3
0.5747	Remote Similarity	NPD4250	Approved
0.5747	Remote Similarity	NPD4251	Approved
0.573	Remote Similarity	NPD7136	Phase 2
0.5729	Remote Similarity	NPD4754	Approved
0.5729	Remote Similarity	NPD5174	Approved
0.5729	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD4787	Phase 1
0.5714	Remote Similarity	NPD4691	Approved
0.5714	Remote Similarity	NPD6001	Approved
0.5714	Remote Similarity	NPD6939	Phase 2
0.5714	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4687	Approved
0.5682	Remote Similarity	NPD5737	Approved
0.5682	Remote Similarity	NPD6672	Approved
0.567	Remote Similarity	NPD5141	Approved
0.5657	Remote Similarity	NPD7320	Approved
0.5657	Remote Similarity	NPD6899	Approved
0.5657	Remote Similarity	NPD6881	Approved
0.5638	Remote Similarity	NPD7638	Approved
0.5634	Remote Similarity	NPD3198	Approved
0.5632	Remote Similarity	NPD4249	Approved
0.5612	Remote Similarity	NPD4768	Approved
0.5612	Remote Similarity	NPD4767	Approved
0.56	Remote Similarity	NPD6373	Approved
0.56	Remote Similarity	NPD6372	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