NPASS Compound

Structure

NPC110725 OpenBabel07101719142D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -4.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.8660 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 -1.7321 -2.0000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 1.7321 -2.0000 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 -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 -2.5981 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 14 2 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 13 21 2 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.17
Volume:	339.359
LogP:	4.163
LogD:	2.434
LogS:	-4.087
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	4.132
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.769
MDCK Permeability:	2.047008092631586e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	94.32028198242188%
Volume Distribution (VD):	1.011
Pgp-substrate:	3.369561195373535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.309
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.672
CYP2C19-substrate:	0.635
CYP2C9-inhibitor:	0.785
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.258
CYP2D6-substrate:	0.477
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	3.473
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.2
Skin Sensitization:	0.214
Carcinogencity:	0.494
Eye Corrosion:	0.003
Eye Irritation:	0.784
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC110725

Natural Product ID:	NPC110725
*Common Name:**	11-Hydroxy-5,7,9,13-Abietatetraene-2,12-Dione
IUPAC Name:	(4aR)-5-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-2,4-dihydrophenanthrene-3,6-dione
Synonyms:
Standard InCHIKey:	VRXNUYDBZCMQCD-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H24O3/c1-11(2)14-8-12-6-7-15-19(3,4)9-13(21)10-20(15,5)16(12)18(23)17(14)22/h6-8,11,23H,9-10H2,1-5H3/t20-/m1/s1
SMILES:	O=C1CC(C)(C)C2=CC=C3C(=C(O)C(=O)C(=C3)C(C)C)[C@@]2(C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1807753
PubChem CID:	56659752
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
NPO33238	pygmacopremna herbacea	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[21708464]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	27.6	ug.mL-1	PMID[548126]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	17.6	ug.mL-1	PMID[548126]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	38.2	ug.mL-1	PMID[548126]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[548126]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	15.6	ug.mL-1	PMID[548126]

☑ 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 NPC110725 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	163
0.1-0.2	1085
0.2-0.3	6310
0.3-0.4	16043
0.4-0.5	11137
0.5-0.6	5594
0.6-0.7	1995
0.7-0.8	341
0.8-0.85	18
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9589	High Similarity	NPC27817
0.9079	High Similarity	NPC225515
0.8947	High Similarity	NPC108955
0.8933	High Similarity	NPC189485
0.8919	High Similarity	NPC1254
0.8873	High Similarity	NPC474060
0.8861	High Similarity	NPC32037
0.8831	High Similarity	NPC55869
0.8533	High Similarity	NPC175079
0.8481	Intermediate Similarity	NPC103486
0.8462	Intermediate Similarity	NPC287063
0.8421	Intermediate Similarity	NPC92080
0.84	Intermediate Similarity	NPC147438
0.8395	Intermediate Similarity	NPC8518
0.8395	Intermediate Similarity	NPC132228
0.8395	Intermediate Similarity	NPC263997
0.8354	Intermediate Similarity	NPC470034
0.8354	Intermediate Similarity	NPC99308
0.8354	Intermediate Similarity	NPC475863
0.8219	Intermediate Similarity	NPC310992
0.8205	Intermediate Similarity	NPC30321
0.8182	Intermediate Similarity	NPC26504
0.8171	Intermediate Similarity	NPC33881
0.8171	Intermediate Similarity	NPC6185
0.8171	Intermediate Similarity	NPC241512
0.8148	Intermediate Similarity	NPC53733
0.8148	Intermediate Similarity	NPC105803
0.8125	Intermediate Similarity	NPC121984
0.8125	Intermediate Similarity	NPC474085
0.8077	Intermediate Similarity	NPC283087
0.8	Intermediate Similarity	NPC112454
0.8	Intermediate Similarity	NPC65615
0.8	Intermediate Similarity	NPC474918
0.8	Intermediate Similarity	NPC68148
0.7973	Intermediate Similarity	NPC260474
0.7973	Intermediate Similarity	NPC188292
0.7952	Intermediate Similarity	NPC255174
0.7952	Intermediate Similarity	NPC33663
0.7952	Intermediate Similarity	NPC474680
0.7949	Intermediate Similarity	NPC470525
0.7949	Intermediate Similarity	NPC292589
0.7949	Intermediate Similarity	NPC112680
0.7931	Intermediate Similarity	NPC263780
0.7927	Intermediate Similarity	NPC102197
0.7901	Intermediate Similarity	NPC116797
0.7895	Intermediate Similarity	NPC474539
0.7848	Intermediate Similarity	NPC165711
0.7816	Intermediate Similarity	NPC174167
0.7816	Intermediate Similarity	NPC470036
0.7808	Intermediate Similarity	NPC251118
0.7778	Intermediate Similarity	NPC476809
0.7778	Intermediate Similarity	NPC477830
0.7778	Intermediate Similarity	NPC74086
0.7778	Intermediate Similarity	NPC2482
0.775	Intermediate Similarity	NPC476808
0.775	Intermediate Similarity	NPC74410
0.7738	Intermediate Similarity	NPC469993
0.7738	Intermediate Similarity	NPC470177
0.7738	Intermediate Similarity	NPC133652
0.7733	Intermediate Similarity	NPC87141
0.7727	Intermediate Similarity	NPC211230
0.7722	Intermediate Similarity	NPC309399
0.7722	Intermediate Similarity	NPC180886
0.7701	Intermediate Similarity	NPC129913
0.7692	Intermediate Similarity	NPC213223
0.7683	Intermediate Similarity	NPC6663
0.7683	Intermediate Similarity	NPC278459
0.7683	Intermediate Similarity	NPC475833
0.7674	Intermediate Similarity	NPC58271
0.7674	Intermediate Similarity	NPC72397
0.7674	Intermediate Similarity	NPC53454
0.7671	Intermediate Similarity	NPC150162
0.7654	Intermediate Similarity	NPC192329
0.7654	Intermediate Similarity	NPC472490
0.7647	Intermediate Similarity	NPC472974
0.7647	Intermediate Similarity	NPC94666
0.764	Intermediate Similarity	NPC23170
0.764	Intermediate Similarity	NPC474882
0.764	Intermediate Similarity	NPC474328
0.7625	Intermediate Similarity	NPC97377
0.7619	Intermediate Similarity	NPC237712
0.7619	Intermediate Similarity	NPC87552
0.7619	Intermediate Similarity	NPC53385
0.7619	Intermediate Similarity	NPC144258
0.759	Intermediate Similarity	NPC302661
0.759	Intermediate Similarity	NPC238991
0.7561	Intermediate Similarity	NPC26139
0.7561	Intermediate Similarity	NPC472478
0.7561	Intermediate Similarity	NPC18955
0.7558	Intermediate Similarity	NPC136548
0.7556	Intermediate Similarity	NPC777
0.7556	Intermediate Similarity	NPC147232
0.7534	Intermediate Similarity	NPC53109
0.7534	Intermediate Similarity	NPC143168
0.7534	Intermediate Similarity	NPC288253
0.7532	Intermediate Similarity	NPC251929
0.7532	Intermediate Similarity	NPC2634
0.7532	Intermediate Similarity	NPC265782
0.7531	Intermediate Similarity	NPC275494
0.7531	Intermediate Similarity	NPC62336
0.7531	Intermediate Similarity	NPC475994
0.7531	Intermediate Similarity	NPC471409
0.7529	Intermediate Similarity	NPC90287
0.7529	Intermediate Similarity	NPC474537
0.7528	Intermediate Similarity	NPC250575
0.7528	Intermediate Similarity	NPC134826
0.75	Intermediate Similarity	NPC309309
0.75	Intermediate Similarity	NPC49019
0.75	Intermediate Similarity	NPC168188
0.75	Intermediate Similarity	NPC83569
0.75	Intermediate Similarity	NPC470015
0.75	Intermediate Similarity	NPC474209
0.75	Intermediate Similarity	NPC263582
0.75	Intermediate Similarity	NPC155198
0.75	Intermediate Similarity	NPC291999
0.75	Intermediate Similarity	NPC127582
0.75	Intermediate Similarity	NPC69279
0.75	Intermediate Similarity	NPC475823
0.747	Intermediate Similarity	NPC44963
0.747	Intermediate Similarity	NPC473217
0.747	Intermediate Similarity	NPC471898
0.747	Intermediate Similarity	NPC472684
0.747	Intermediate Similarity	NPC189237
0.7468	Intermediate Similarity	NPC301065
0.7442	Intermediate Similarity	NPC327115
0.7442	Intermediate Similarity	NPC222613
0.7442	Intermediate Similarity	NPC475022
0.7442	Intermediate Similarity	NPC203795
0.7442	Intermediate Similarity	NPC118648
0.7439	Intermediate Similarity	NPC170793
0.7439	Intermediate Similarity	NPC476177
0.7439	Intermediate Similarity	NPC19900
0.7439	Intermediate Similarity	NPC474113
0.7436	Intermediate Similarity	NPC54123
0.7436	Intermediate Similarity	NPC181204
0.7436	Intermediate Similarity	NPC84790
0.7432	Intermediate Similarity	NPC7029
0.7432	Intermediate Similarity	NPC4638
0.7416	Intermediate Similarity	NPC99380
0.7416	Intermediate Similarity	NPC45579
0.7416	Intermediate Similarity	NPC204341
0.7412	Intermediate Similarity	NPC473246
0.7412	Intermediate Similarity	NPC476412
0.7407	Intermediate Similarity	NPC266193
0.7407	Intermediate Similarity	NPC257666
0.7403	Intermediate Similarity	NPC469914
0.7403	Intermediate Similarity	NPC256846
0.7403	Intermediate Similarity	NPC139397
0.7386	Intermediate Similarity	NPC210216
0.7381	Intermediate Similarity	NPC260956
0.7381	Intermediate Similarity	NPC48362
0.7381	Intermediate Similarity	NPC142253
0.7381	Intermediate Similarity	NPC3511
0.7381	Intermediate Similarity	NPC320514
0.7381	Intermediate Similarity	NPC193347
0.7375	Intermediate Similarity	NPC473171
0.7375	Intermediate Similarity	NPC476346
0.7363	Intermediate Similarity	NPC295347
0.7363	Intermediate Similarity	NPC280725
0.7356	Intermediate Similarity	NPC470523
0.7356	Intermediate Similarity	NPC220930
0.7356	Intermediate Similarity	NPC272039
0.7349	Intermediate Similarity	NPC469637
0.7342	Intermediate Similarity	NPC247586
0.7342	Intermediate Similarity	NPC56747
0.7342	Intermediate Similarity	NPC303613
0.7342	Intermediate Similarity	NPC130016
0.7342	Intermediate Similarity	NPC474228
0.7342	Intermediate Similarity	NPC470045
0.7342	Intermediate Similarity	NPC470044
0.7342	Intermediate Similarity	NPC180015
0.7342	Intermediate Similarity	NPC153660
0.7342	Intermediate Similarity	NPC109576
0.7326	Intermediate Similarity	NPC469948
0.7326	Intermediate Similarity	NPC94531
0.7326	Intermediate Similarity	NPC29447
0.7326	Intermediate Similarity	NPC11711
0.7326	Intermediate Similarity	NPC123319
0.7326	Intermediate Similarity	NPC311702
0.7326	Intermediate Similarity	NPC476426
0.7317	Intermediate Similarity	NPC207772
0.7308	Intermediate Similarity	NPC307176
0.7308	Intermediate Similarity	NPC260040
0.7297	Intermediate Similarity	NPC197238
0.7297	Intermediate Similarity	NPC202118
0.7294	Intermediate Similarity	NPC258985
0.7294	Intermediate Similarity	NPC70834
0.7294	Intermediate Similarity	NPC288281
0.7284	Intermediate Similarity	NPC186554
0.7284	Intermediate Similarity	NPC250621
0.7284	Intermediate Similarity	NPC69143
0.7284	Intermediate Similarity	NPC76966
0.7273	Intermediate Similarity	NPC470524
0.7273	Intermediate Similarity	NPC307298
0.7273	Intermediate Similarity	NPC471722
0.7273	Intermediate Similarity	NPC320665
0.7262	Intermediate Similarity	NPC90055
0.7262	Intermediate Similarity	NPC4166
0.7262	Intermediate Similarity	NPC201912
0.7262	Intermediate Similarity	NPC142244

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 NPC110725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1411
0.2-0.3	4145
0.3-0.4	2473
0.4-0.5	596
0.5-0.6	234
0.6-0.7	107
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8701	High Similarity	NPD4695	Discontinued
0.8072	Intermediate Similarity	NPD5279	Phase 3
0.8072	Intermediate Similarity	NPD5280	Approved
0.8072	Intermediate Similarity	NPD4694	Approved
0.8	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5276	Approved
0.7857	Intermediate Similarity	NPD5690	Phase 2
0.7778	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3617	Approved
0.7692	Intermediate Similarity	NPD4687	Approved
0.7692	Intermediate Similarity	NPD4058	Approved
0.7692	Intermediate Similarity	NPD5733	Approved
0.7619	Intermediate Similarity	NPD4197	Approved
0.7534	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4691	Approved
0.7529	Intermediate Similarity	NPD5329	Approved
0.7403	Intermediate Similarity	NPD4137	Phase 3
0.7381	Intermediate Similarity	NPD4221	Approved
0.7381	Intermediate Similarity	NPD4223	Phase 3
0.7333	Intermediate Similarity	NPD5133	Approved
0.7308	Intermediate Similarity	NPD4747	Approved
0.7303	Intermediate Similarity	NPD4096	Approved
0.7273	Intermediate Similarity	NPD4518	Approved
0.7237	Intermediate Similarity	NPD7331	Phase 2
0.7222	Intermediate Similarity	NPD5281	Approved
0.7222	Intermediate Similarity	NPD5284	Approved
0.7209	Intermediate Similarity	NPD3665	Phase 1
0.7209	Intermediate Similarity	NPD3133	Approved
0.7209	Intermediate Similarity	NPD3666	Approved
0.7191	Intermediate Similarity	NPD4753	Phase 2
0.7176	Intermediate Similarity	NPD3667	Approved
0.7111	Intermediate Similarity	NPD5692	Phase 3
0.7093	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4138	Approved
0.7045	Intermediate Similarity	NPD4689	Approved
0.7045	Intermediate Similarity	NPD5205	Approved
0.7045	Intermediate Similarity	NPD4690	Approved
0.7045	Intermediate Similarity	NPD3618	Phase 1
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4693	Phase 3
0.7045	Intermediate Similarity	NPD4688	Approved
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7033	Intermediate Similarity	NPD6050	Approved
0.7033	Intermediate Similarity	NPD5694	Approved
0.7011	Intermediate Similarity	NPD4786	Approved
0.6989	Remote Similarity	NPD5210	Approved
0.6989	Remote Similarity	NPD4629	Approved
0.6989	Remote Similarity	NPD5695	Phase 3
0.6988	Remote Similarity	NPD4756	Discovery
0.6915	Remote Similarity	NPD5222	Approved
0.6915	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5221	Approved
0.6883	Remote Similarity	NPD7341	Phase 2
0.6848	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD5173	Approved
0.6835	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4195	Approved
0.6813	Remote Similarity	NPD5328	Approved
0.6795	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1696	Phase 3
0.6739	Remote Similarity	NPD5207	Approved
0.6737	Remote Similarity	NPD4697	Phase 3
0.6703	Remote Similarity	NPD5737	Approved
0.6703	Remote Similarity	NPD6672	Approved
0.6701	Remote Similarity	NPD5286	Approved
0.6701	Remote Similarity	NPD4696	Approved
0.6701	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD8028	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6633	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD5654	Approved
0.663	Remote Similarity	NPD6080	Approved
0.663	Remote Similarity	NPD6904	Approved
0.663	Remote Similarity	NPD6673	Approved
0.6629	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD5696	Approved
0.6596	Remote Similarity	NPD4202	Approved
0.6593	Remote Similarity	NPD3573	Approved
0.6582	Remote Similarity	NPD3704	Approved
0.6566	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD5091	Approved
0.6566	Remote Similarity	NPD4633	Approved
0.6566	Remote Similarity	NPD5225	Approved
0.6566	Remote Similarity	NPD5226	Approved
0.6562	Remote Similarity	NPD7614	Phase 1
0.6533	Remote Similarity	NPD287	Approved
0.6531	Remote Similarity	NPD6404	Discontinued
0.6531	Remote Similarity	NPD4700	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6517	Remote Similarity	NPD4788	Approved
0.65	Remote Similarity	NPD5175	Approved
0.65	Remote Similarity	NPD5174	Approved
0.6495	Remote Similarity	NPD5959	Approved
0.6489	Remote Similarity	NPD5693	Phase 1
0.6489	Remote Similarity	NPD6411	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD6098	Approved
0.6484	Remote Similarity	NPD7146	Approved
0.6436	Remote Similarity	NPD5141	Approved
0.6421	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD5282	Discontinued
0.6353	Remote Similarity	NPD8264	Approved
0.6344	Remote Similarity	NPD5208	Approved
0.6344	Remote Similarity	NPD6903	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4754	Approved
0.6327	Remote Similarity	NPD7902	Approved
0.6311	Remote Similarity	NPD5697	Approved
0.6282	Remote Similarity	NPD4193	Approved
0.6282	Remote Similarity	NPD4194	Approved
0.6282	Remote Similarity	NPD4192	Approved
0.6282	Remote Similarity	NPD4191	Approved
0.6277	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD5168	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6222	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4767	Approved
0.6214	Remote Similarity	NPD6675	Approved
0.6214	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD4768	Approved
0.6214	Remote Similarity	NPD5739	Approved
0.6214	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6013	Approved
0.6186	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5701	Approved
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6132	Remote Similarity	NPD5135	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6132	Remote Similarity	NPD5169	Approved
0.6132	Remote Similarity	NPD5247	Approved
0.6132	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4634	Approved
0.6132	Remote Similarity	NPD5249	Phase 3
0.6132	Remote Similarity	NPD5248	Approved
0.6132	Remote Similarity	NPD5251	Approved
0.6132	Remote Similarity	NPD5250	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6092	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6617	Approved
0.6075	Remote Similarity	NPD6650	Approved
0.6075	Remote Similarity	NPD5127	Approved
0.6075	Remote Similarity	NPD6649	Approved
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD6847	Approved
0.6075	Remote Similarity	NPD5216	Approved
0.6075	Remote Similarity	NPD5215	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6075	Remote Similarity	NPD5217	Approved
0.6071	Remote Similarity	NPD7144	Approved
0.6071	Remote Similarity	NPD7143	Approved
0.6061	Remote Similarity	NPD7732	Phase 3
0.6047	Remote Similarity	NPD4785	Approved
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.6047	Remote Similarity	NPD4784	Approved
0.604	Remote Similarity	NPD2066	Phase 3
0.6038	Remote Similarity	NPD6372	Approved
0.6038	Remote Similarity	NPD6373	Approved
0.6022	Remote Similarity	NPD1694	Approved
0.602	Remote Similarity	NPD6001	Approved
0.602	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7900	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD3495	Discontinued
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD4243	Approved
0.6	Remote Similarity	NPD7150	Approved
0.5977	Remote Similarity	NPD8039	Approved
0.5977	Remote Similarity	NPD6942	Approved
0.5977	Remote Similarity	NPD7339	Approved
0.5974	Remote Similarity	NPD8779	Phase 3
0.5963	Remote Similarity	NPD4632	Approved
0.596	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4627	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