NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.19
Volume:	280.487
LogP:	2.955
LogD:	2.691
LogS:	-3.515
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.812
Synthetic Accessibility Score:	4.164
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.689
MDCK Permeability:	1.8058013665722683e-05
Pgp-inhibitor:	0.3
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	82.15637969970703%
Volume Distribution (VD):	0.627
Pgp-substrate:	23.104167938232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.637
CYP2C19-inhibitor:	0.286
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.323
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.279
CYP3A4-substrate:	0.628

ADMET: Excretion

Clearance (CL):	7.797
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.209
Carcinogencity:	0.224
Eye Corrosion:	0.044
Eye Irritation:	0.176
Respiratory Toxicity:	0.418

Download Data

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

Natural Product: NPC144627

Natural Product ID:	NPC144627
*Common Name:**	(3As,7Ar)-5-(2-Hydroxy-2-Methylpropyl)-3A,6,7A-Trimethyl-1,2,3,7-Tetrahydroinden-4-One
IUPAC Name:	(3aS,7aR)-5-(2-hydroxy-2-methylpropyl)-3a,6,7a-trimethyl-1,2,3,7-tetrahydroinden-4-one
Synonyms:
Standard InCHIKey:	WZZYQRAVLUJPDZ-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C16H26O2/c1-11-9-15(4)7-6-8-16(15,5)13(17)12(11)10-14(2,3)18/h18H,6-10H2,1-5H3/t15-,16-/m1/s1
SMILES:	CC1=C(CC(C)(C)O)C(=O)[C@@]2(C)CCC[C@]2(C)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573329
PubChem CID:	25156424
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
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18980381]
NPO27646	Cystoseira baccata	Species	Sargassaceae	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	3
MIC	7
Others	2

Activity Type	# Activity
Organism	9
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6233	Organism	Sargassum muticum	Sargassum muticum	IC50	=	1.0	ug.mL-1	PMID[551913]
NPT6641	Organism	Ulva intestinalis	Ulva intestinalis	IC50	=	1.0	ug.mL-1	PMID[551913]
NPT2	Others	Unspecified		IC50	=	1.0	ug.mL-1	PMID[551913]
NPT6357	Organism	Pseudoalteromonas elyakovii	Pseudoalteromonas elyakovii	MIC	>	100.0	ug.mL-1	PMID[551913]
NPT6384	Organism	Vibrio aestuarianus	Vibrio aestuarianus	MIC	>	100.0	ug.mL-1	PMID[551913]
NPT6359	Organism	Polaribacter irgensii	Polaribacter irgensii	MIC	>	100.0	ug.mL-1	PMID[551913]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[551913]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[551913]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[551913]
NPT6415	Organism	Exanthemachrysis gayraliae	Exanthemachrysis gayraliae	MIC	=	1.0	ug.mL-1	PMID[551913]
NPT27	Others	Unspecified		LC50	>	100.0	ug.mL-1	PMID[551913]

☑ 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 NPC144627 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	165
0.1-0.2	1552
0.2-0.3	9599
0.3-0.4	15140
0.4-0.5	7602
0.5-0.6	6220
0.6-0.7	2131
0.7-0.8	280
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8205	Intermediate Similarity	NPC193347
0.8133	Intermediate Similarity	NPC92080
0.8101	Intermediate Similarity	NPC472492
0.8077	Intermediate Similarity	NPC477372
0.8077	Intermediate Similarity	NPC136150
0.8	Intermediate Similarity	NPC61473
0.8	Intermediate Similarity	NPC144258
0.8	Intermediate Similarity	NPC251435
0.8	Intermediate Similarity	NPC472480
0.7949	Intermediate Similarity	NPC279667
0.7922	Intermediate Similarity	NPC471409
0.7922	Intermediate Similarity	NPC30321
0.7922	Intermediate Similarity	NPC476808
0.7922	Intermediate Similarity	NPC275494
0.7901	Intermediate Similarity	NPC15838
0.7901	Intermediate Similarity	NPC132629
0.7901	Intermediate Similarity	NPC469948
0.7875	Intermediate Similarity	NPC470015
0.7875	Intermediate Similarity	NPC168188
0.7867	Intermediate Similarity	NPC470299
0.7848	Intermediate Similarity	NPC150506
0.7838	Intermediate Similarity	NPC84790
0.7821	Intermediate Similarity	NPC477371
0.7821	Intermediate Similarity	NPC215843
0.7805	Intermediate Similarity	NPC474733
0.7805	Intermediate Similarity	NPC31564
0.7805	Intermediate Similarity	NPC474732
0.7805	Intermediate Similarity	NPC474778
0.7805	Intermediate Similarity	NPC472488
0.7805	Intermediate Similarity	NPC472491
0.7805	Intermediate Similarity	NPC472494
0.7805	Intermediate Similarity	NPC472479
0.7805	Intermediate Similarity	NPC145879
0.7792	Intermediate Similarity	NPC257666
0.7792	Intermediate Similarity	NPC266193
0.7778	Intermediate Similarity	NPC161423
0.7778	Intermediate Similarity	NPC321187
0.7778	Intermediate Similarity	NPC85774
0.7778	Intermediate Similarity	NPC209882
0.7778	Intermediate Similarity	NPC58841
0.7778	Intermediate Similarity	NPC237712
0.7778	Intermediate Similarity	NPC214043
0.7778	Intermediate Similarity	NPC473246
0.7778	Intermediate Similarity	NPC329043
0.7778	Intermediate Similarity	NPC227064
0.7763	Intermediate Similarity	NPC175079
0.775	Intermediate Similarity	NPC260956
0.775	Intermediate Similarity	NPC477269
0.775	Intermediate Similarity	NPC469325
0.775	Intermediate Similarity	NPC320514
0.775	Intermediate Similarity	NPC133391
0.775	Intermediate Similarity	NPC477270
0.775	Intermediate Similarity	NPC151519
0.775	Intermediate Similarity	NPC129080
0.775	Intermediate Similarity	NPC477271
0.7733	Intermediate Similarity	NPC247586
0.7722	Intermediate Similarity	NPC108955
0.7722	Intermediate Similarity	NPC2482
0.7722	Intermediate Similarity	NPC469637
0.7722	Intermediate Similarity	NPC45495
0.7722	Intermediate Similarity	NPC476809
0.7711	Intermediate Similarity	NPC475740
0.7711	Intermediate Similarity	NPC99909
0.7711	Intermediate Similarity	NPC472481
0.7711	Intermediate Similarity	NPC472484
0.7711	Intermediate Similarity	NPC472482
0.7711	Intermediate Similarity	NPC136548
0.7711	Intermediate Similarity	NPC472493
0.7711	Intermediate Similarity	NPC136948
0.7711	Intermediate Similarity	NPC58063
0.7692	Intermediate Similarity	NPC19443
0.7692	Intermediate Similarity	NPC74410
0.7683	Intermediate Similarity	NPC473038
0.7683	Intermediate Similarity	NPC197823
0.7683	Intermediate Similarity	NPC94531
0.7683	Intermediate Similarity	NPC123319
0.7683	Intermediate Similarity	NPC29447
0.7683	Intermediate Similarity	NPC311702
0.7662	Intermediate Similarity	NPC470525
0.7662	Intermediate Similarity	NPC186554
0.7662	Intermediate Similarity	NPC76966
0.7662	Intermediate Similarity	NPC180886
0.7654	Intermediate Similarity	NPC62214
0.7654	Intermediate Similarity	NPC477373
0.7625	Intermediate Similarity	NPC147066
0.7625	Intermediate Similarity	NPC55869
0.7625	Intermediate Similarity	NPC121984
0.7625	Intermediate Similarity	NPC201912
0.7625	Intermediate Similarity	NPC226068
0.7625	Intermediate Similarity	NPC38350
0.7619	Intermediate Similarity	NPC471722
0.7619	Intermediate Similarity	NPC472483
0.7595	Intermediate Similarity	NPC7232
0.7595	Intermediate Similarity	NPC472490
0.7595	Intermediate Similarity	NPC192329
0.7595	Intermediate Similarity	NPC32758
0.7595	Intermediate Similarity	NPC229204
0.7595	Intermediate Similarity	NPC301769
0.759	Intermediate Similarity	NPC327115
0.759	Intermediate Similarity	NPC222613
0.759	Intermediate Similarity	NPC72133
0.759	Intermediate Similarity	NPC475022
0.759	Intermediate Similarity	NPC118648
0.7568	Intermediate Similarity	NPC469914
0.7564	Intermediate Similarity	NPC165711
0.7564	Intermediate Similarity	NPC137547
0.7564	Intermediate Similarity	NPC34110
0.7561	Intermediate Similarity	NPC221758
0.7561	Intermediate Similarity	NPC59453
0.7534	Intermediate Similarity	NPC476626
0.7532	Intermediate Similarity	NPC77501
0.7532	Intermediate Similarity	NPC114236
0.7529	Intermediate Similarity	NPC472477
0.7529	Intermediate Similarity	NPC326627
0.7529	Intermediate Similarity	NPC268406
0.7529	Intermediate Similarity	NPC1015
0.7529	Intermediate Similarity	NPC477943
0.7529	Intermediate Similarity	NPC26959
0.7529	Intermediate Similarity	NPC472475
0.7529	Intermediate Similarity	NPC310010
0.7529	Intermediate Similarity	NPC472489
0.7529	Intermediate Similarity	NPC119416
0.7529	Intermediate Similarity	NPC186688
0.7529	Intermediate Similarity	NPC31985
0.7529	Intermediate Similarity	NPC262043
0.75	Intermediate Similarity	NPC18955
0.75	Intermediate Similarity	NPC93778
0.75	Intermediate Similarity	NPC472478
0.7471	Intermediate Similarity	NPC25750
0.7471	Intermediate Similarity	NPC233118
0.7471	Intermediate Similarity	NPC474807
0.747	Intermediate Similarity	NPC179006
0.747	Intermediate Similarity	NPC474853
0.747	Intermediate Similarity	NPC474218
0.747	Intermediate Similarity	NPC470574
0.747	Intermediate Similarity	NPC142649
0.7468	Intermediate Similarity	NPC189485
0.7468	Intermediate Similarity	NPC207772
0.7468	Intermediate Similarity	NPC469996
0.7468	Intermediate Similarity	NPC23778
0.7468	Intermediate Similarity	NPC475994
0.7467	Intermediate Similarity	NPC173321
0.7467	Intermediate Similarity	NPC280256
0.7442	Intermediate Similarity	NPC472476
0.7442	Intermediate Similarity	NPC48010
0.7439	Intermediate Similarity	NPC477852
0.7439	Intermediate Similarity	NPC278648
0.7439	Intermediate Similarity	NPC69279
0.7439	Intermediate Similarity	NPC310470
0.7439	Intermediate Similarity	NPC470165
0.7439	Intermediate Similarity	NPC476082
0.7439	Intermediate Similarity	NPC105803
0.7439	Intermediate Similarity	NPC83569
0.7439	Intermediate Similarity	NPC97913
0.7436	Intermediate Similarity	NPC151622
0.7436	Intermediate Similarity	NPC472305
0.7436	Intermediate Similarity	NPC215481
0.7436	Intermediate Similarity	NPC263582
0.7436	Intermediate Similarity	NPC182848
0.7436	Intermediate Similarity	NPC7629
0.7436	Intermediate Similarity	NPC239758
0.7436	Intermediate Similarity	NPC469646
0.7412	Intermediate Similarity	NPC474677
0.7412	Intermediate Similarity	NPC143767
0.7412	Intermediate Similarity	NPC328539
0.7412	Intermediate Similarity	NPC320665
0.7412	Intermediate Similarity	NPC131470
0.7407	Intermediate Similarity	NPC278459
0.7407	Intermediate Similarity	NPC473217
0.7407	Intermediate Similarity	NPC471898
0.7407	Intermediate Similarity	NPC44963
0.7407	Intermediate Similarity	NPC472684
0.7407	Intermediate Similarity	NPC225515
0.7403	Intermediate Similarity	NPC167049
0.7403	Intermediate Similarity	NPC469691
0.7397	Intermediate Similarity	NPC103734
0.7381	Intermediate Similarity	NPC89077
0.7381	Intermediate Similarity	NPC20688
0.7381	Intermediate Similarity	NPC51014
0.7381	Intermediate Similarity	NPC94666
0.7381	Intermediate Similarity	NPC6247
0.7375	Intermediate Similarity	NPC274996
0.7375	Intermediate Similarity	NPC196827
0.7375	Intermediate Similarity	NPC474113
0.7368	Intermediate Similarity	NPC469737
0.7361	Intermediate Similarity	NPC212210
0.7356	Intermediate Similarity	NPC204341
0.7356	Intermediate Similarity	NPC475806
0.7356	Intermediate Similarity	NPC19114
0.7349	Intermediate Similarity	NPC251170
0.7349	Intermediate Similarity	NPC472265
0.7349	Intermediate Similarity	NPC7927
0.7349	Intermediate Similarity	NPC164577
0.7349	Intermediate Similarity	NPC82902
0.7349	Intermediate Similarity	NPC230527
0.7342	Intermediate Similarity	NPC472014
0.7342	Intermediate Similarity	NPC97377
0.7342	Intermediate Similarity	NPC197659
0.7333	Intermediate Similarity	NPC139397
0.7326	Intermediate Similarity	NPC76879

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 NPC144627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2389
0.2-0.3	4250
0.3-0.4	1632
0.4-0.5	337
0.5-0.6	233
0.6-0.7	109
0.7-0.8	29
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
0.84	Intermediate Similarity	NPD3617	Approved
0.8205	Intermediate Similarity	NPD4223	Phase 3
0.8205	Intermediate Similarity	NPD4221	Approved
0.8025	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7341	Phase 2
0.8	Intermediate Similarity	NPD4197	Approved
0.7901	Intermediate Similarity	NPD5329	Approved
0.7848	Intermediate Similarity	NPD4139	Approved
0.7848	Intermediate Similarity	NPD4692	Approved
0.7805	Intermediate Similarity	NPD5280	Approved
0.7805	Intermediate Similarity	NPD4693	Phase 3
0.7805	Intermediate Similarity	NPD5205	Approved
0.7805	Intermediate Similarity	NPD4689	Approved
0.7805	Intermediate Similarity	NPD3618	Phase 1
0.7805	Intermediate Similarity	NPD4138	Approved
0.7805	Intermediate Similarity	NPD4690	Approved
0.7805	Intermediate Similarity	NPD5690	Phase 2
0.7805	Intermediate Similarity	NPD4694	Approved
0.7805	Intermediate Similarity	NPD4688	Approved
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD3133	Approved
0.775	Intermediate Similarity	NPD3667	Approved
0.7639	Intermediate Similarity	NPD7331	Phase 2
0.7561	Intermediate Similarity	NPD4786	Approved
0.7558	Intermediate Similarity	NPD5284	Approved
0.7558	Intermediate Similarity	NPD5281	Approved
0.7529	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7412	Intermediate Similarity	NPD4518	Approved
0.7381	Intermediate Similarity	NPD4519	Discontinued
0.7381	Intermediate Similarity	NPD5279	Phase 3
0.7381	Intermediate Similarity	NPD4623	Approved
0.7375	Intermediate Similarity	NPD4195	Approved
0.7333	Intermediate Similarity	NPD4137	Phase 3
0.7326	Intermediate Similarity	NPD5328	Approved
0.7303	Intermediate Similarity	NPD5210	Approved
0.7303	Intermediate Similarity	NPD4629	Approved
0.7273	Intermediate Similarity	NPD4202	Approved
0.7273	Intermediate Similarity	NPD5133	Approved
0.7241	Intermediate Similarity	NPD4096	Approved
0.7237	Intermediate Similarity	NPD4691	Approved
0.7237	Intermediate Similarity	NPD4747	Approved
0.7159	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD3668	Phase 3
0.7111	Intermediate Similarity	NPD5695	Phase 3
0.7079	Intermediate Similarity	NPD6399	Phase 3
0.7065	Intermediate Similarity	NPD5696	Approved
0.7045	Intermediate Similarity	NPD5207	Approved
0.7033	Intermediate Similarity	NPD4697	Phase 3
0.7024	Intermediate Similarity	NPD4788	Approved
0.7011	Intermediate Similarity	NPD5208	Approved
0.6986	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5330	Approved
0.6977	Remote Similarity	NPD6684	Approved
0.6977	Remote Similarity	NPD7521	Approved
0.6977	Remote Similarity	NPD6409	Approved
0.6977	Remote Similarity	NPD7146	Approved
0.6977	Remote Similarity	NPD7334	Approved
0.6962	Remote Similarity	NPD4687	Approved
0.6962	Remote Similarity	NPD4058	Approved
0.6962	Remote Similarity	NPD5733	Approved
0.6957	Remote Similarity	NPD4755	Approved
0.6957	Remote Similarity	NPD6084	Phase 2
0.6957	Remote Similarity	NPD6083	Phase 2
0.6932	Remote Similarity	NPD6673	Approved
0.6932	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6904	Approved
0.6932	Remote Similarity	NPD6080	Approved
0.6923	Remote Similarity	NPD5276	Approved
0.686	Remote Similarity	NPD1696	Phase 3
0.6854	Remote Similarity	NPD5692	Phase 3
0.6848	Remote Similarity	NPD5221	Approved
0.6848	Remote Similarity	NPD5222	Approved
0.6848	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5091	Approved
0.6818	Remote Similarity	NPD5737	Approved
0.6818	Remote Similarity	NPD6672	Approved
0.6818	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6001	Approved
0.6809	Remote Similarity	NPD4700	Approved
0.6809	Remote Similarity	NPD4696	Approved
0.6809	Remote Similarity	NPD5286	Approved
0.6809	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6098	Approved
0.6778	Remote Similarity	NPD5693	Phase 1
0.6778	Remote Similarity	NPD6050	Approved
0.6778	Remote Similarity	NPD5694	Approved
0.6774	Remote Similarity	NPD5173	Approved
0.6753	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5360	Phase 3
0.675	Remote Similarity	NPD4784	Approved
0.675	Remote Similarity	NPD4785	Approved
0.6739	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5223	Approved
0.6711	Remote Similarity	NPD3704	Approved
0.6709	Remote Similarity	NPD4243	Approved
0.6706	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.663	Remote Similarity	NPD5282	Discontinued
0.6598	Remote Similarity	NPD4754	Approved
0.6598	Remote Similarity	NPD5174	Approved
0.6598	Remote Similarity	NPD5175	Approved
0.6593	Remote Similarity	NPD7515	Phase 2
0.6588	Remote Similarity	NPD5369	Approved
0.6585	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5654	Approved
0.6531	Remote Similarity	NPD5141	Approved
0.6517	Remote Similarity	NPD3573	Approved
0.65	Remote Similarity	NPD4758	Discontinued
0.6494	Remote Similarity	NPD4224	Phase 2
0.6484	Remote Similarity	NPD5785	Approved
0.6477	Remote Similarity	NPD5363	Approved
0.6477	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD4748	Discontinued
0.6465	Remote Similarity	NPD5739	Approved
0.6465	Remote Similarity	NPD7128	Approved
0.6465	Remote Similarity	NPD6675	Approved
0.6465	Remote Similarity	NPD6402	Approved
0.6465	Remote Similarity	NPD4768	Approved
0.6465	Remote Similarity	NPD4767	Approved
0.6463	Remote Similarity	NPD4190	Phase 3
0.6463	Remote Similarity	NPD6942	Approved
0.6463	Remote Similarity	NPD7339	Approved
0.6463	Remote Similarity	NPD5275	Approved
0.6456	Remote Similarity	NPD3698	Phase 2
0.6456	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7748	Approved
0.6438	Remote Similarity	NPD287	Approved
0.6436	Remote Similarity	NPD6372	Approved
0.6436	Remote Similarity	NPD6373	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7902	Approved
0.6421	Remote Similarity	NPD5959	Approved
0.64	Remote Similarity	NPD5701	Approved
0.64	Remote Similarity	NPD5697	Approved
0.6375	Remote Similarity	NPD4244	Approved
0.6375	Remote Similarity	NPD4789	Approved
0.6375	Remote Similarity	NPD4245	Approved
0.6341	Remote Similarity	NPD6926	Approved
0.6341	Remote Similarity	NPD6924	Approved
0.6337	Remote Similarity	NPD6011	Approved
0.6337	Remote Similarity	NPD5128	Approved
0.6337	Remote Similarity	NPD4730	Approved
0.6337	Remote Similarity	NPD6881	Approved
0.6337	Remote Similarity	NPD4729	Approved
0.6337	Remote Similarity	NPD6899	Approved
0.6337	Remote Similarity	NPD7320	Approved
0.6322	Remote Similarity	NPD4269	Approved
0.6322	Remote Similarity	NPD4270	Approved
0.6316	Remote Similarity	NPD7614	Phase 1
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6650	Approved
0.63	Remote Similarity	NPD6008	Approved
0.6296	Remote Similarity	NPD6081	Approved
0.6296	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6404	Discontinued
0.6279	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6012	Approved
0.6275	Remote Similarity	NPD6014	Approved
0.6275	Remote Similarity	NPD6013	Approved
0.6263	Remote Similarity	NPD6052	Approved
0.625	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD5135	Approved
0.6214	Remote Similarity	NPD7290	Approved
0.6214	Remote Similarity	NPD6883	Approved
0.6214	Remote Similarity	NPD5247	Approved
0.6214	Remote Similarity	NPD5251	Approved
0.6214	Remote Similarity	NPD5248	Approved
0.6214	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5250	Approved
0.6214	Remote Similarity	NPD4634	Approved
0.6214	Remote Similarity	NPD7102	Approved
0.6214	Remote Similarity	NPD5169	Approved
0.6214	Remote Similarity	NPD5249	Phase 3
0.619	Remote Similarity	NPD6933	Approved
0.6176	Remote Similarity	NPD5168	Approved
0.6168	Remote Similarity	NPD7115	Discovery
0.6154	Remote Similarity	NPD5217	Approved
0.6154	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD5216	Approved
0.6154	Remote Similarity	NPD5127	Approved
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5215	Approved
0.6136	Remote Similarity	NPD4752	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