NPASS Compound

Structure

NPC159325 OpenBabel07101719512D 33 37 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 30 1 0 0 0 0 15 30 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 25 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 1 0 0 0 20 32 2 0 0 0 0 21 26 1 1 0 0 0 21 29 1 0 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 29 1 1 0 0 0 24 33 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	4.905
LogD:	4.062
LogS:	-4.464
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	5.066
Fsp3:	0.967
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:	-4.887
MDCK Permeability:	1.1391027328500059e-05
Pgp-inhibitor:	0.775
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.692
Plasma Protein Binding (PPB):	92.05330657958984%
Volume Distribution (VD):	1.092
Pgp-substrate:	2.863198757171631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	11.316
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.59
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.531
Maximum Recommended Daily Dose:	0.759
Skin Sensitization:	0.269
Carcinogencity:	0.348
Eye Corrosion:	0.014
Eye Irritation:	0.017
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC159325

Natural Product ID:	NPC159325
*Common Name:**	6Beta,28-Dihydroxyfriedelan-3-One
IUPAC Name:	(4R,4aS,5R,6aS,6aS,6bR,8aS,12aS,14aR,14bS)-5-hydroxy-8a-(hydroxymethyl)-4,4a,6a,6b,11,11,14a-heptamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
Synonyms:	28-Hydroxyzelanol
Standard InCHIKey:	JEDNEJGSAFQCKK-RBZPDDGOSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-19-20(32)8-9-21-26(4)11-12-28(6)23-17-25(2,3)10-14-30(23,18-31)15-13-27(28,5)22(26)16-24(33)29(19,21)7/h19,21-24,31,33H,8-18H2,1-7H3/t19-,21-,22-,23-,24+,26-,27+,28-,29+,30+/m0/s1
SMILES:	OC[C@@]12CCC(C[C@H]2[C@]2([C@@](CC1)(C)[C@H]1C[C@@H](O)[C@]3([C@H]([C@@]1(CC2)C)CCC(=O)[C@@H]3C)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480271
PubChem CID:	44575290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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	9

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[473085]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[473085]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[473085]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[473085]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[473085]
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	13.0	ug ml-1	PMID[473085]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[473085]

☑ 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 NPC159325 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	426
0.1-0.2	3709
0.2-0.3	14260
0.3-0.4	11902
0.4-0.5	5019
0.5-0.6	4423
0.6-0.7	2269
0.7-0.8	604
0.8-0.85	39
0.85-0.9	29
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168511
0.9853	High Similarity	NPC282905
0.9853	High Similarity	NPC68426
0.9853	High Similarity	NPC477229
0.9714	High Similarity	NPC108840
0.9571	High Similarity	NPC267753
0.9429	High Similarity	NPC130011
0.9265	High Similarity	NPC2568
0.9265	High Similarity	NPC180777
0.9265	High Similarity	NPC260319
0.9265	High Similarity	NPC103647
0.9178	High Similarity	NPC472608
0.9067	High Similarity	NPC50658
0.9041	High Similarity	NPC23884
0.9028	High Similarity	NPC195155
0.9028	High Similarity	NPC174964
0.9028	High Similarity	NPC97534
0.9014	High Similarity	NPC81759
0.8919	High Similarity	NPC26029
0.8904	High Similarity	NPC475742
0.8904	High Similarity	NPC5767
0.8873	High Similarity	NPC247195
0.8873	High Similarity	NPC89310
0.8873	High Similarity	NPC290058
0.8816	High Similarity	NPC48756
0.8816	High Similarity	NPC280781
0.8784	High Similarity	NPC221420
0.875	High Similarity	NPC232112
0.8718	High Similarity	NPC25037
0.8718	High Similarity	NPC34984
0.8714	High Similarity	NPC475977
0.8667	High Similarity	NPC31031
0.8667	High Similarity	NPC243594
0.8649	High Similarity	NPC472487
0.8649	High Similarity	NPC472486
0.8611	High Similarity	NPC58057
0.8611	High Similarity	NPC320549
0.8611	High Similarity	NPC156277
0.8611	High Similarity	NPC151018
0.8608	High Similarity	NPC62572
0.8592	High Similarity	NPC131892
0.8592	High Similarity	NPC213178
0.8592	High Similarity	NPC6120
0.8592	High Similarity	NPC327728
0.8571	High Similarity	NPC472984
0.8571	High Similarity	NPC476071
0.8533	High Similarity	NPC298168
0.8533	High Similarity	NPC143133
0.8529	High Similarity	NPC292419
0.8529	High Similarity	NPC290791
0.8514	High Similarity	NPC125767
0.8514	High Similarity	NPC21220
0.8514	High Similarity	NPC273366
0.8481	Intermediate Similarity	NPC105895
0.8451	Intermediate Similarity	NPC31187
0.8451	Intermediate Similarity	NPC474954
0.8451	Intermediate Similarity	NPC281203
0.8451	Intermediate Similarity	NPC100917
0.8451	Intermediate Similarity	NPC469724
0.8378	Intermediate Similarity	NPC254340
0.831	Intermediate Similarity	NPC204233
0.8289	Intermediate Similarity	NPC472746
0.8289	Intermediate Similarity	NPC475031
0.8272	Intermediate Similarity	NPC74363
0.8272	Intermediate Similarity	NPC475862
0.8267	Intermediate Similarity	NPC212733
0.8267	Intermediate Similarity	NPC159789
0.825	Intermediate Similarity	NPC475745
0.825	Intermediate Similarity	NPC474482
0.8228	Intermediate Similarity	NPC61107
0.8228	Intermediate Similarity	NPC30583
0.8228	Intermediate Similarity	NPC289486
0.8194	Intermediate Similarity	NPC475893
0.8194	Intermediate Similarity	NPC469987
0.8171	Intermediate Similarity	NPC73064
0.8158	Intermediate Similarity	NPC4209
0.8148	Intermediate Similarity	NPC133954
0.8133	Intermediate Similarity	NPC133922
0.8133	Intermediate Similarity	NPC167702
0.8133	Intermediate Similarity	NPC280026
0.8125	Intermediate Similarity	NPC472743
0.8125	Intermediate Similarity	NPC475726
0.8125	Intermediate Similarity	NPC269684
0.8101	Intermediate Similarity	NPC271572
0.8101	Intermediate Similarity	NPC474870
0.8101	Intermediate Similarity	NPC328264
0.8082	Intermediate Similarity	NPC321732
0.8082	Intermediate Similarity	NPC324607
0.8077	Intermediate Similarity	NPC320144
0.8077	Intermediate Similarity	NPC73013
0.8052	Intermediate Similarity	NPC112463
0.8052	Intermediate Similarity	NPC207010
0.8052	Intermediate Similarity	NPC317913
0.8049	Intermediate Similarity	NPC472738
0.8049	Intermediate Similarity	NPC213412
0.8049	Intermediate Similarity	NPC187545
0.8028	Intermediate Similarity	NPC260116
0.8028	Intermediate Similarity	NPC80463
0.8025	Intermediate Similarity	NPC474996
0.8025	Intermediate Similarity	NPC219535
0.8025	Intermediate Similarity	NPC237938
0.8025	Intermediate Similarity	NPC473299
0.8	Intermediate Similarity	NPC475230
0.8	Intermediate Similarity	NPC268040
0.8	Intermediate Similarity	NPC310766
0.7975	Intermediate Similarity	NPC261616
0.7975	Intermediate Similarity	NPC470609
0.7949	Intermediate Similarity	NPC80089
0.7949	Intermediate Similarity	NPC185465
0.7949	Intermediate Similarity	NPC224802
0.7949	Intermediate Similarity	NPC34046
0.7949	Intermediate Similarity	NPC324700
0.7949	Intermediate Similarity	NPC171426
0.7945	Intermediate Similarity	NPC473225
0.7927	Intermediate Similarity	NPC292553
0.7917	Intermediate Similarity	NPC142712
0.7907	Intermediate Similarity	NPC472148
0.7907	Intermediate Similarity	NPC472147
0.7882	Intermediate Similarity	NPC291028
0.7882	Intermediate Similarity	NPC185529
0.7882	Intermediate Similarity	NPC472146
0.7875	Intermediate Similarity	NPC469745
0.7875	Intermediate Similarity	NPC58631
0.7857	Intermediate Similarity	NPC131104
0.7857	Intermediate Similarity	NPC472739
0.7857	Intermediate Similarity	NPC474719
0.7857	Intermediate Similarity	NPC473319
0.7857	Intermediate Similarity	NPC3032
0.7857	Intermediate Similarity	NPC230387
0.7848	Intermediate Similarity	NPC201276
0.7848	Intermediate Similarity	NPC80891
0.7831	Intermediate Similarity	NPC83242
0.7831	Intermediate Similarity	NPC477579
0.7831	Intermediate Similarity	NPC72638
0.7831	Intermediate Similarity	NPC471737
0.7831	Intermediate Similarity	NPC235341
0.7831	Intermediate Similarity	NPC95594
0.7808	Intermediate Similarity	NPC48079
0.7808	Intermediate Similarity	NPC41542
0.7805	Intermediate Similarity	NPC171789
0.7805	Intermediate Similarity	NPC180834
0.7805	Intermediate Similarity	NPC474233
0.7805	Intermediate Similarity	NPC264665
0.7805	Intermediate Similarity	NPC74595
0.7792	Intermediate Similarity	NPC179858
0.7791	Intermediate Similarity	NPC105189
0.7778	Intermediate Similarity	NPC328007
0.7778	Intermediate Similarity	NPC230047
0.7778	Intermediate Similarity	NPC19311
0.7778	Intermediate Similarity	NPC317066
0.7765	Intermediate Similarity	NPC69627
0.7765	Intermediate Similarity	NPC471459
0.7765	Intermediate Similarity	NPC67653
0.7763	Intermediate Similarity	NPC253805
0.7763	Intermediate Similarity	NPC211009
0.7738	Intermediate Similarity	NPC307426
0.7738	Intermediate Similarity	NPC68160
0.7738	Intermediate Similarity	NPC98442
0.7738	Intermediate Similarity	NPC88716
0.7738	Intermediate Similarity	NPC130577
0.7738	Intermediate Similarity	NPC171203
0.7738	Intermediate Similarity	NPC293564
0.7738	Intermediate Similarity	NPC142415
0.7738	Intermediate Similarity	NPC57469
0.7738	Intermediate Similarity	NPC51700
0.7738	Intermediate Similarity	NPC102683
0.7738	Intermediate Similarity	NPC4643
0.7738	Intermediate Similarity	NPC18064
0.7738	Intermediate Similarity	NPC242468
0.7733	Intermediate Similarity	NPC476731
0.7733	Intermediate Similarity	NPC108131
0.7711	Intermediate Similarity	NPC294438
0.7711	Intermediate Similarity	NPC264317
0.7711	Intermediate Similarity	NPC131350
0.7703	Intermediate Similarity	NPC472741
0.7683	Intermediate Similarity	NPC327451
0.7674	Intermediate Similarity	NPC477872
0.7674	Intermediate Similarity	NPC18536
0.7674	Intermediate Similarity	NPC475211
0.7674	Intermediate Similarity	NPC120968
0.7674	Intermediate Similarity	NPC273621
0.7674	Intermediate Similarity	NPC88337
0.7674	Intermediate Similarity	NPC18872
0.7674	Intermediate Similarity	NPC50443
0.7674	Intermediate Similarity	NPC210037
0.7674	Intermediate Similarity	NPC7260
0.7674	Intermediate Similarity	NPC193750
0.7674	Intermediate Similarity	NPC227467
0.7674	Intermediate Similarity	NPC290614
0.7662	Intermediate Similarity	NPC472854
0.7662	Intermediate Similarity	NPC38426
0.7662	Intermediate Similarity	NPC162164
0.7654	Intermediate Similarity	NPC3915
0.7654	Intermediate Similarity	NPC12933
0.7647	Intermediate Similarity	NPC474512
0.7647	Intermediate Similarity	NPC181225
0.7647	Intermediate Similarity	NPC470629
0.7647	Intermediate Similarity	NPC17733
0.7647	Intermediate Similarity	NPC472802
0.7647	Intermediate Similarity	NPC246708

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 NPC159325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	521
0.1-0.2	3866
0.2-0.3	3355
0.3-0.4	893
0.4-0.5	253
0.5-0.6	201
0.6-0.7	34
0.7-0.8	23
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8611	High Similarity	NPD4809	Clinical (unspecified phase)
0.8611	High Similarity	NPD4808	Clinical (unspecified phase)
0.8592	High Similarity	NPD3699	Clinical (unspecified phase)
0.8592	High Similarity	NPD3700	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD3703	Phase 2
0.8219	Intermediate Similarity	NPD4245	Approved
0.8219	Intermediate Similarity	NPD4244	Approved
0.8158	Intermediate Similarity	NPD6117	Approved
0.8133	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3698	Phase 2
0.8052	Intermediate Similarity	NPD6116	Phase 1
0.7973	Intermediate Similarity	NPD4789	Approved
0.7949	Intermediate Similarity	NPD6115	Approved
0.7949	Intermediate Similarity	NPD6118	Approved
0.7949	Intermediate Similarity	NPD6697	Approved
0.7949	Intermediate Similarity	NPD6114	Approved
0.7945	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD5360	Phase 3
0.7778	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3671	Phase 1
0.7711	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7515	Phase 2
0.7432	Intermediate Similarity	NPD4224	Phase 2
0.7403	Intermediate Similarity	NPD4758	Discontinued
0.7222	Intermediate Similarity	NPD7748	Approved
0.7209	Intermediate Similarity	NPD3618	Phase 1
0.7191	Intermediate Similarity	NPD8034	Phase 2
0.7191	Intermediate Similarity	NPD8035	Phase 2
0.7179	Intermediate Similarity	NPD5777	Approved
0.7179	Intermediate Similarity	NPD6081	Approved
0.7174	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5364	Discontinued
0.6988	Remote Similarity	NPD7645	Phase 2
0.6977	Remote Similarity	NPD4786	Approved
0.6966	Remote Similarity	NPD5328	Approved
0.6941	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD4788	Approved
0.6848	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7900	Approved
0.6835	Remote Similarity	NPD4787	Phase 1
0.6813	Remote Similarity	NPD6079	Approved
0.6707	Remote Similarity	NPD3702	Approved
0.6591	Remote Similarity	NPD3666	Approved
0.6591	Remote Similarity	NPD3665	Phase 1
0.6591	Remote Similarity	NPD3133	Approved
0.6559	Remote Similarity	NPD4202	Approved
0.6526	Remote Similarity	NPD4697	Phase 3
0.64	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD5221	Approved
0.6354	Remote Similarity	NPD5222	Approved
0.6354	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8418	Phase 2
0.6324	Remote Similarity	NPD385	Approved
0.6324	Remote Similarity	NPD384	Approved
0.6322	Remote Similarity	NPD7525	Registered
0.6322	Remote Similarity	NPD6928	Phase 2
0.6311	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4755	Approved
0.6289	Remote Similarity	NPD5173	Approved
0.6279	Remote Similarity	NPD3617	Approved
0.6264	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3668	Phase 3
0.6184	Remote Similarity	NPD3198	Approved
0.6176	Remote Similarity	NPD6920	Discontinued
0.6162	Remote Similarity	NPD4700	Approved
0.6162	Remote Similarity	NPD5286	Approved
0.6162	Remote Similarity	NPD5285	Approved
0.6162	Remote Similarity	NPD4696	Approved
0.6129	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5223	Approved
0.6087	Remote Similarity	NPD5279	Phase 3
0.6064	Remote Similarity	NPD4753	Phase 2
0.6061	Remote Similarity	NPD7638	Approved
0.6058	Remote Similarity	NPD6415	Discontinued
0.6058	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5224	Approved
0.604	Remote Similarity	NPD5225	Approved
0.604	Remote Similarity	NPD5226	Approved
0.604	Remote Similarity	NPD4633	Approved
0.604	Remote Similarity	NPD5211	Phase 2
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD6373	Approved
0.598	Remote Similarity	NPD4754	Approved
0.598	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD5175	Approved
0.5978	Remote Similarity	NPD5329	Approved
0.5955	Remote Similarity	NPD4695	Discontinued
0.593	Remote Similarity	NPD6942	Approved
0.593	Remote Similarity	NPD7339	Approved
0.5922	Remote Similarity	NPD5141	Approved
0.5918	Remote Similarity	NPD5210	Approved
0.5918	Remote Similarity	NPD4629	Approved
0.5914	Remote Similarity	NPD6684	Approved
0.5914	Remote Similarity	NPD5330	Approved
0.5914	Remote Similarity	NPD7146	Approved
0.5914	Remote Similarity	NPD7521	Approved
0.5914	Remote Similarity	NPD6409	Approved
0.5914	Remote Similarity	NPD7334	Approved
0.5905	Remote Similarity	NPD6881	Approved
0.5905	Remote Similarity	NPD6899	Approved
0.5905	Remote Similarity	NPD7320	Approved
0.5889	Remote Similarity	NPD4692	Approved
0.5889	Remote Similarity	NPD4139	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD7632	Discontinued
0.5877	Remote Similarity	NPD8328	Phase 3
0.5875	Remote Similarity	NPD7909	Approved
0.587	Remote Similarity	NPD4197	Approved
0.5865	Remote Similarity	NPD4767	Approved
0.5865	Remote Similarity	NPD4768	Approved
0.5862	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7614	Phase 1
0.5851	Remote Similarity	NPD3573	Approved
0.581	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD5697	Approved
0.58	Remote Similarity	NPD6084	Phase 2
0.58	Remote Similarity	NPD6083	Phase 2
0.5794	Remote Similarity	NPD6883	Approved
0.5794	Remote Similarity	NPD7290	Approved
0.5794	Remote Similarity	NPD7102	Approved
0.5789	Remote Similarity	NPD6903	Approved
0.5783	Remote Similarity	NPD6705	Phase 1
0.578	Remote Similarity	NPD8133	Approved
0.5766	Remote Similarity	NPD7115	Discovery
0.5755	Remote Similarity	NPD4729	Approved
0.5755	Remote Similarity	NPD5128	Approved
0.5755	Remote Similarity	NPD4730	Approved
0.5755	Remote Similarity	NPD5168	Approved
0.5755	Remote Similarity	NPD6011	Approved
0.5745	Remote Similarity	NPD4138	Approved
0.5745	Remote Similarity	NPD4693	Phase 3
0.5745	Remote Similarity	NPD4519	Discontinued
0.5745	Remote Similarity	NPD5205	Approved
0.5745	Remote Similarity	NPD4623	Approved
0.5745	Remote Similarity	NPD4690	Approved
0.5745	Remote Similarity	NPD4689	Approved
0.5745	Remote Similarity	NPD4688	Approved
0.5741	Remote Similarity	NPD6617	Approved
0.5741	Remote Similarity	NPD8130	Phase 1
0.5741	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6869	Approved
0.5741	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD8171	Discontinued
0.5701	Remote Similarity	NPD6013	Approved
0.5701	Remote Similarity	NPD6014	Approved
0.5701	Remote Similarity	NPD6012	Approved
0.5688	Remote Similarity	NPD8297	Approved
0.5688	Remote Similarity	NPD6882	Approved
0.5679	Remote Similarity	NPD371	Approved
0.567	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.567	Remote Similarity	NPD6700	Approved
0.566	Remote Similarity	NPD6412	Phase 2
0.5648	Remote Similarity	NPD5250	Approved
0.5648	Remote Similarity	NPD5169	Approved
0.5648	Remote Similarity	NPD5249	Phase 3
0.5648	Remote Similarity	NPD5251	Approved
0.5648	Remote Similarity	NPD5248	Approved
0.5648	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5247	Approved
0.5648	Remote Similarity	NPD4634	Approved
0.5648	Remote Similarity	NPD5135	Approved
0.5636	Remote Similarity	NPD8298	Phase 2
0.5625	Remote Similarity	NPD6672	Approved
0.5625	Remote Similarity	NPD5737	Approved
0.5612	Remote Similarity	NPD6702	Approved
0.5612	Remote Similarity	NPD6411	Approved
0.5612	Remote Similarity	NPD6703	Approved
0.5604	Remote Similarity	NPD4748	Discontinued
0.56	Remote Similarity	NPD6356	Clinical (unspecified phase)

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