NPASS Compound

Structure

NPC231739 OpenBabel07101719252D 26 26 0 0 1 0 0 0 0 0999 V2000 -4.6790 12.3840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6449 12.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3520 11.9357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0932 10.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8003 10.2627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5415 9.2968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2486 8.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9897 7.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0238 7.3649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7650 6.3990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7991 6.1402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5403 5.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 4.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 3.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3496 3.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0908 2.7247 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 -1.1248 2.4659 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 -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 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -1.6594 0.8912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 25 1 1 0 0 0 23 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.3
Volume:	416.269
LogP:	5.724
LogD:	4.144
LogS:	-4.133
# Rotatable Bonds:	15
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	3.214
Fsp3:	0.826
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.787
MDCK Permeability:	3.229070716770366e-05
Pgp-inhibitor:	0.161
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	98.244140625%
Volume Distribution (VD):	0.569
Pgp-substrate:	0.9105390906333923%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.321
CYP2C19-substrate:	0.322
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	7.546
Half-life (T1/2):	0.417

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.943
Carcinogencity:	0.278
Eye Corrosion:	0.11
Eye Irritation:	0.702
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC231739

Natural Product ID:	NPC231739
*Common Name:**	(4R,6R)-Dihydroxy-4-[10(Z)-Heptadecenyl]-2-Cyclohexenone
IUPAC Name:	(4R,6S)-4-[(Z)-heptadec-10-enyl]-4,6-dihydroxycyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	QGMORWLDWJPVQC-CHXUTICSSA-N
Standard InCHI:	InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-23(26)19-17-21(24)22(25)20-23/h7-8,17,19,22,25-26H,2-6,9-16,18,20H2,1H3/b8-7-/t22-,23-/m0/s1
SMILES:	CCCCCC/C=CCCCCCCCCC[C@@]1(C=CC(=O)[C@H](C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506497
PubChem CID:	10021708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514013]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	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
IC50	7

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	4.4	ug.mL-1	PMID[491591]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	1.8	ug.mL-1	PMID[491591]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[491591]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[491591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.3	ug.mL-1	PMID[491591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.1	ug.mL-1	PMID[491591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.2	ug.mL-1	PMID[491591]

☑ 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 NPC231739 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	176
0.1-0.2	1188
0.2-0.3	6023
0.3-0.4	14221
0.4-0.5	11709
0.5-0.6	6312
0.6-0.7	2683
0.7-0.8	364
0.8-0.85	12
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC477786
0.9351	High Similarity	NPC477784
0.9351	High Similarity	NPC477785
0.8571	High Similarity	NPC471061
0.8267	Intermediate Similarity	NPC107848
0.8228	Intermediate Similarity	NPC475994
0.8228	Intermediate Similarity	NPC478122
0.8193	Intermediate Similarity	NPC187529
0.8101	Intermediate Similarity	NPC97173
0.8101	Intermediate Similarity	NPC82666
0.8	Intermediate Similarity	NPC192006
0.7931	Intermediate Similarity	NPC477684
0.7901	Intermediate Similarity	NPC19900
0.7875	Intermediate Similarity	NPC476007
0.7867	Intermediate Similarity	NPC106613
0.7831	Intermediate Similarity	NPC158411
0.7831	Intermediate Similarity	NPC38796
0.7791	Intermediate Similarity	NPC472007
0.775	Intermediate Similarity	NPC477708
0.7727	Intermediate Similarity	NPC471399
0.7674	Intermediate Similarity	NPC472009
0.7674	Intermediate Similarity	NPC472974
0.7674	Intermediate Similarity	NPC94666
0.7671	Intermediate Similarity	NPC269737
0.7662	Intermediate Similarity	NPC469914
0.766	Intermediate Similarity	NPC87351
0.7654	Intermediate Similarity	NPC473536
0.7647	Intermediate Similarity	NPC476412
0.7625	Intermediate Similarity	NPC474885
0.7619	Intermediate Similarity	NPC279186
0.7595	Intermediate Similarity	NPC275098
0.7595	Intermediate Similarity	NPC186042
0.7595	Intermediate Similarity	NPC29542
0.7595	Intermediate Similarity	NPC323437
0.7595	Intermediate Similarity	NPC201562
0.759	Intermediate Similarity	NPC470946
0.759	Intermediate Similarity	NPC470945
0.759	Intermediate Similarity	NPC470947
0.7586	Intermediate Similarity	NPC471738
0.7582	Intermediate Similarity	NPC476245
0.7579	Intermediate Similarity	NPC311612
0.7579	Intermediate Similarity	NPC111323
0.7568	Intermediate Similarity	NPC477830
0.7564	Intermediate Similarity	NPC94743
0.7564	Intermediate Similarity	NPC291062
0.7564	Intermediate Similarity	NPC173321
0.7561	Intermediate Similarity	NPC321180
0.7558	Intermediate Similarity	NPC28887
0.7558	Intermediate Similarity	NPC476426
0.7531	Intermediate Similarity	NPC271070
0.7531	Intermediate Similarity	NPC474197
0.7531	Intermediate Similarity	NPC279537
0.7528	Intermediate Similarity	NPC265856
0.7528	Intermediate Similarity	NPC166554
0.75	Intermediate Similarity	NPC472008
0.75	Intermediate Similarity	NPC470298
0.75	Intermediate Similarity	NPC137163
0.75	Intermediate Similarity	NPC227814
0.75	Intermediate Similarity	NPC112868
0.75	Intermediate Similarity	NPC275766
0.75	Intermediate Similarity	NPC144995
0.7471	Intermediate Similarity	NPC194417
0.7471	Intermediate Similarity	NPC196381
0.747	Intermediate Similarity	NPC136033
0.747	Intermediate Similarity	NPC113363
0.747	Intermediate Similarity	NPC308038
0.747	Intermediate Similarity	NPC281138
0.7468	Intermediate Similarity	NPC474884
0.7467	Intermediate Similarity	NPC7029
0.7444	Intermediate Similarity	NPC472978
0.7442	Intermediate Similarity	NPC31086
0.7442	Intermediate Similarity	NPC7927
0.7442	Intermediate Similarity	NPC472326
0.7442	Intermediate Similarity	NPC230527
0.7439	Intermediate Similarity	NPC211279
0.7439	Intermediate Similarity	NPC281296
0.7436	Intermediate Similarity	NPC10758
0.7436	Intermediate Similarity	NPC143396
0.7436	Intermediate Similarity	NPC250928
0.7436	Intermediate Similarity	NPC262673
0.7419	Intermediate Similarity	NPC20066
0.7416	Intermediate Similarity	NPC472973
0.7412	Intermediate Similarity	NPC7414
0.7412	Intermediate Similarity	NPC474252
0.7407	Intermediate Similarity	NPC474011
0.7403	Intermediate Similarity	NPC278895
0.7403	Intermediate Similarity	NPC269985
0.7396	Intermediate Similarity	NPC247957
0.7396	Intermediate Similarity	NPC249187
0.7386	Intermediate Similarity	NPC179659
0.7386	Intermediate Similarity	NPC287079
0.7381	Intermediate Similarity	NPC271104
0.7381	Intermediate Similarity	NPC172013
0.7381	Intermediate Similarity	NPC74086
0.7368	Intermediate Similarity	NPC474329
0.7368	Intermediate Similarity	NPC474304
0.7363	Intermediate Similarity	NPC469692
0.7363	Intermediate Similarity	NPC469645
0.7363	Intermediate Similarity	NPC125180
0.7363	Intermediate Similarity	NPC474736
0.7356	Intermediate Similarity	NPC77971
0.7356	Intermediate Similarity	NPC32037
0.7356	Intermediate Similarity	NPC261380
0.7356	Intermediate Similarity	NPC179006
0.7356	Intermediate Similarity	NPC474853
0.7356	Intermediate Similarity	NPC125290
0.7349	Intermediate Similarity	NPC471409
0.7349	Intermediate Similarity	NPC267231
0.7349	Intermediate Similarity	NPC62336
0.7349	Intermediate Similarity	NPC275494
0.7349	Intermediate Similarity	NPC121200
0.7347	Intermediate Similarity	NPC185
0.7342	Intermediate Similarity	NPC286154
0.734	Intermediate Similarity	NPC300584
0.7333	Intermediate Similarity	NPC143168
0.7333	Intermediate Similarity	NPC53109
0.7326	Intermediate Similarity	NPC251475
0.7326	Intermediate Similarity	NPC169941
0.7317	Intermediate Similarity	NPC151622
0.7317	Intermediate Similarity	NPC7629
0.7317	Intermediate Similarity	NPC469646
0.7317	Intermediate Similarity	NPC470525
0.7317	Intermediate Similarity	NPC263582
0.7308	Intermediate Similarity	NPC146376
0.7308	Intermediate Similarity	NPC263382
0.7308	Intermediate Similarity	NPC125578
0.7308	Intermediate Similarity	NPC45264
0.7303	Intermediate Similarity	NPC471791
0.7303	Intermediate Similarity	NPC87189
0.7303	Intermediate Similarity	NPC53454
0.7303	Intermediate Similarity	NPC228415
0.7303	Intermediate Similarity	NPC471793
0.7294	Intermediate Similarity	NPC88735
0.7294	Intermediate Similarity	NPC325031
0.7294	Intermediate Similarity	NPC47031
0.7292	Intermediate Similarity	NPC39996
0.7284	Intermediate Similarity	NPC215050
0.7284	Intermediate Similarity	NPC122244
0.7284	Intermediate Similarity	NPC227396
0.7284	Intermediate Similarity	NPC264178
0.7283	Intermediate Similarity	NPC78159
0.7283	Intermediate Similarity	NPC472976
0.7283	Intermediate Similarity	NPC121825
0.7283	Intermediate Similarity	NPC472977
0.7283	Intermediate Similarity	NPC217624
0.7283	Intermediate Similarity	NPC181393
0.7273	Intermediate Similarity	NPC475461
0.7273	Intermediate Similarity	NPC183736
0.7273	Intermediate Similarity	NPC16119
0.7273	Intermediate Similarity	NPC316426
0.7273	Intermediate Similarity	NPC476982
0.7273	Intermediate Similarity	NPC197089
0.7273	Intermediate Similarity	NPC315395
0.7273	Intermediate Similarity	NPC305475
0.7273	Intermediate Similarity	NPC261721
0.7253	Intermediate Similarity	NPC476705
0.7253	Intermediate Similarity	NPC475441
0.7253	Intermediate Similarity	NPC146852
0.7253	Intermediate Similarity	NPC142838
0.7253	Intermediate Similarity	NPC475806
0.725	Intermediate Similarity	NPC84790
0.725	Intermediate Similarity	NPC319163
0.725	Intermediate Similarity	NPC67076
0.7245	Intermediate Similarity	NPC257353
0.7241	Intermediate Similarity	NPC295799
0.7241	Intermediate Similarity	NPC40687
0.7241	Intermediate Similarity	NPC96259
0.7241	Intermediate Similarity	NPC141193
0.7234	Intermediate Similarity	NPC266842
0.7229	Intermediate Similarity	NPC34110
0.7229	Intermediate Similarity	NPC86917
0.7229	Intermediate Similarity	NPC320630
0.7229	Intermediate Similarity	NPC116177
0.7229	Intermediate Similarity	NPC74995
0.7229	Intermediate Similarity	NPC7563
0.7222	Intermediate Similarity	NPC472983
0.7222	Intermediate Similarity	NPC310236
0.7222	Intermediate Similarity	NPC123912
0.7222	Intermediate Similarity	NPC471054
0.7222	Intermediate Similarity	NPC212598
0.7215	Intermediate Similarity	NPC136473
0.7215	Intermediate Similarity	NPC94488
0.7209	Intermediate Similarity	NPC93590
0.7209	Intermediate Similarity	NPC145963
0.7209	Intermediate Similarity	NPC475690
0.7209	Intermediate Similarity	NPC85772
0.7209	Intermediate Similarity	NPC103486
0.7204	Intermediate Similarity	NPC180950
0.7204	Intermediate Similarity	NPC272617
0.7204	Intermediate Similarity	NPC91408
0.72	Intermediate Similarity	NPC214644
0.7195	Intermediate Similarity	NPC199445
0.7195	Intermediate Similarity	NPC114236
0.7195	Intermediate Similarity	NPC472256
0.7195	Intermediate Similarity	NPC60718
0.7191	Intermediate Similarity	NPC72513
0.7188	Intermediate Similarity	NPC470184
0.7188	Intermediate Similarity	NPC115862
0.7179	Intermediate Similarity	NPC474619
0.7179	Intermediate Similarity	NPC26500

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 NPC231739 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	1787
0.2-0.3	3960
0.3-0.4	2238
0.4-0.5	626
0.5-0.6	274
0.6-0.7	91
0.7-0.8	12
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
0.7765	Intermediate Similarity	NPD5363	Approved
0.7733	Intermediate Similarity	NPD7331	Phase 2
0.7412	Intermediate Similarity	NPD4269	Approved
0.7412	Intermediate Similarity	NPD4270	Approved
0.7381	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5785	Approved
0.7333	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4756	Discovery
0.7176	Intermediate Similarity	NPD4822	Approved
0.7176	Intermediate Similarity	NPD4821	Approved
0.7176	Intermediate Similarity	NPD4820	Approved
0.7176	Intermediate Similarity	NPD4252	Approved
0.7176	Intermediate Similarity	NPD4819	Approved
0.7159	Intermediate Similarity	NPD1696	Phase 3
0.7143	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7341	Phase 2
0.7126	Intermediate Similarity	NPD7154	Phase 3
0.7093	Intermediate Similarity	NPD5369	Approved
0.7079	Intermediate Similarity	NPD5786	Approved
0.7051	Intermediate Similarity	NPD3704	Approved
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.7013	Intermediate Similarity	NPD3197	Phase 1
0.6977	Remote Similarity	NPD4695	Discontinued
0.6941	Remote Similarity	NPD4271	Approved
0.6941	Remote Similarity	NPD4268	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6932	Remote Similarity	NPD6110	Phase 1
0.6932	Remote Similarity	NPD5362	Discontinued
0.6915	Remote Similarity	NPD5282	Discontinued
0.6889	Remote Similarity	NPD5279	Phase 3
0.6848	Remote Similarity	NPD4753	Phase 2
0.6809	Remote Similarity	NPD5778	Approved
0.6809	Remote Similarity	NPD5779	Approved
0.68	Remote Similarity	NPD5141	Approved
0.6782	Remote Similarity	NPD5368	Approved
0.6782	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD46	Approved
0.6774	Remote Similarity	NPD6698	Approved
0.6735	Remote Similarity	NPD5285	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6703	Remote Similarity	NPD4623	Approved
0.6703	Remote Similarity	NPD4519	Discontinued
0.6703	Remote Similarity	NPD5690	Phase 2
0.6703	Remote Similarity	NPD3618	Phase 1
0.6702	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6629	Remote Similarity	NPD6435	Approved
0.6629	Remote Similarity	NPD3667	Approved
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.6598	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5222	Approved
0.6593	Remote Similarity	NPD5329	Approved
0.6556	Remote Similarity	NPD5332	Approved
0.6556	Remote Similarity	NPD5331	Approved
0.6538	Remote Similarity	NPD368	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD4755	Approved
0.6531	Remote Similarity	NPD6083	Phase 2
0.6531	Remote Similarity	NPD6084	Phase 2
0.6526	Remote Similarity	NPD7983	Approved
0.6526	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4790	Discontinued
0.65	Remote Similarity	NPD5223	Approved
0.6495	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5370	Suspended
0.6489	Remote Similarity	NPD5328	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4197	Approved
0.6465	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6881	Approved
0.6442	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD4697	Phase 3
0.6429	Remote Similarity	NPD7839	Suspended
0.6422	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6650	Approved
0.6413	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD4700	Approved
0.6395	Remote Similarity	NPD8264	Approved
0.6395	Remote Similarity	NPD8039	Approved
0.6354	Remote Similarity	NPD6411	Approved
0.6354	Remote Similarity	NPD7515	Phase 2
0.6346	Remote Similarity	NPD5697	Approved
0.6346	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4694	Approved
0.6344	Remote Similarity	NPD5280	Approved
0.6341	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5695	Phase 3
0.6321	Remote Similarity	NPD6883	Approved
0.6321	Remote Similarity	NPD6371	Approved
0.6321	Remote Similarity	NPD7290	Approved
0.6321	Remote Similarity	NPD7102	Approved
0.6304	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5696	Approved
0.6289	Remote Similarity	NPD4202	Approved
0.6286	Remote Similarity	NPD4730	Approved
0.6286	Remote Similarity	NPD4729	Approved
0.6277	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD4251	Approved
0.6267	Remote Similarity	NPD3195	Phase 2
0.6267	Remote Similarity	NPD3196	Approved
0.6267	Remote Similarity	NPD3194	Approved
0.6267	Remote Similarity	NPD4266	Approved
0.6264	Remote Similarity	NPD4221	Approved
0.6264	Remote Similarity	NPD4223	Phase 3
0.6262	Remote Similarity	NPD8130	Phase 1
0.6262	Remote Similarity	NPD6869	Approved
0.6262	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6847	Approved
0.6262	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD7128	Approved
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6013	Approved
0.6226	Remote Similarity	NPD6012	Approved
0.6226	Remote Similarity	NPD6014	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.6222	Remote Similarity	NPD7332	Phase 2
0.6222	Remote Similarity	NPD7514	Phase 3
0.6211	Remote Similarity	NPD4518	Approved
0.6204	Remote Similarity	NPD8297	Approved
0.6204	Remote Similarity	NPD6882	Approved
0.6184	Remote Similarity	NPD342	Phase 1
0.6184	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3617	Approved
0.618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3732	Approved
0.617	Remote Similarity	NPD4249	Approved
0.617	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD5249	Phase 3
0.6168	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6163	Remote Similarity	NPD4732	Discontinued
0.6154	Remote Similarity	NPD1237	Approved
0.6146	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4225	Approved
0.6133	Remote Similarity	NPD3172	Approved
0.6132	Remote Similarity	NPD6011	Approved
0.6132	Remote Similarity	NPD5128	Approved
0.6132	Remote Similarity	NPD7320	Approved
0.6122	Remote Similarity	NPD6399	Phase 3
0.6111	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD5216	Approved
0.6111	Remote Similarity	NPD5217	Approved
0.6098	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4767	Approved
0.6095	Remote Similarity	NPD4768	Approved
0.6064	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7748	Approved
0.6058	Remote Similarity	NPD4754	Approved
0.6044	Remote Similarity	NPD6930	Phase 2
0.6044	Remote Similarity	NPD6931	Approved
0.6042	Remote Similarity	NPD6672	Approved
0.6042	Remote Similarity	NPD5737	Approved
0.604	Remote Similarity	NPD7902	Approved
0.6038	Remote Similarity	NPD5701	Approved
0.6022	Remote Similarity	NPD4788	Approved
0.602	Remote Similarity	NPD5284	Approved
0.602	Remote Similarity	NPD5281	Approved
0.602	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD5169	Approved
0.6019	Remote Similarity	NPD5135	Approved
0.6019	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD4138	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD5205	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD4693	Phase 3
0.6	Remote Similarity	NPD4688	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD4690	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD4689	Approved
0.6	Remote Similarity	NPD6409	Approved
0.5981	Remote Similarity	NPD5168	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