NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.13
Volume:	249.412
LogP:	1.645
LogD:	1.04
LogS:	-2.326
# Rotatable Bonds:	2
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.686
Synthetic Accessibility Score:	4.404
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.536
MDCK Permeability:	2.8550837669172324e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.374
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.749
Plasma Protein Binding (PPB):	54.23120880126953%
Volume Distribution (VD):	1.491
Pgp-substrate:	44.04269027709961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	7.458
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.951
Carcinogencity:	0.877
Eye Corrosion:	0.979
Eye Irritation:	0.785
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC474562

Natural Product ID:	NPC474562
*Common Name:**	Panudial
IUPAC Name:	(1R,4aS,8aS)-5,5-dimethyl-8-oxo-1,4,4a,6,7,8a-hexahydronaphthalene-1,2-dicarbaldehyde
Synonyms:	Panudial
Standard InCHIKey:	HIRWQNBXJGMISA-GMXVVIOVSA-N
Standard InCHI:	InChI=1S/C14H18O3/c1-14(2)6-5-12(17)13-10(8-16)9(7-15)3-4-11(13)14/h3,7-8,10-11,13H,4-6H2,1-2H3/t10-,11-,13+/m0/s1
SMILES:	O=C[C@H]1C(=CC[C@H]2[C@@H]1C(=O)CCC2(C)C)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472433
PubChem CID:	160400
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones

*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
NPO33197	panus biosynthesizes	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8148002]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC30	=	2.5	ug ml-1	PMID[453421]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC30	=	6.0	ug ml-1	PMID[453421]

☑ 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 NPC474562 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	191
0.1-0.2	2093
0.2-0.3	11292
0.3-0.4	15188
0.4-0.5	8038
0.5-0.6	4345
0.6-0.7	1312
0.7-0.8	213
0.8-0.85	17
0.85-0.9	2
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC4370
0.9394	High Similarity	NPC290350
0.9254	High Similarity	NPC155198
0.9167	High Similarity	NPC115515
0.8784	High Similarity	NPC90965
0.8611	High Similarity	NPC219232
0.8611	High Similarity	NPC211641
0.8611	High Similarity	NPC128346
0.8551	High Similarity	NPC475523
0.8529	High Similarity	NPC470329
0.8485	Intermediate Similarity	NPC127582
0.8429	Intermediate Similarity	NPC260474
0.8429	Intermediate Similarity	NPC188292
0.8382	Intermediate Similarity	NPC285371
0.8382	Intermediate Similarity	NPC52449
0.8382	Intermediate Similarity	NPC475124
0.8382	Intermediate Similarity	NPC169275
0.8378	Intermediate Similarity	NPC469793
0.8378	Intermediate Similarity	NPC469796
0.8333	Intermediate Similarity	NPC276764
0.8333	Intermediate Similarity	NPC472304
0.8333	Intermediate Similarity	NPC304983
0.8289	Intermediate Similarity	NPC170793
0.8261	Intermediate Similarity	NPC251118
0.8235	Intermediate Similarity	NPC288253
0.8194	Intermediate Similarity	NPC251929
0.8194	Intermediate Similarity	NPC265782
0.8194	Intermediate Similarity	NPC2634
0.8194	Intermediate Similarity	NPC260040
0.8182	Intermediate Similarity	NPC474509
0.8182	Intermediate Similarity	NPC27610
0.8182	Intermediate Similarity	NPC56905
0.8169	Intermediate Similarity	NPC310992
0.8169	Intermediate Similarity	NPC87141
0.8158	Intermediate Similarity	NPC228911
0.8133	Intermediate Similarity	NPC19907
0.8116	Intermediate Similarity	NPC212210
0.8082	Intermediate Similarity	NPC54123
0.8056	Intermediate Similarity	NPC162867
0.8056	Intermediate Similarity	NPC61702
0.8056	Intermediate Similarity	NPC256846
0.8056	Intermediate Similarity	NPC139397
0.8028	Intermediate Similarity	NPC193770
0.7975	Intermediate Similarity	NPC470813
0.7973	Intermediate Similarity	NPC303613
0.7973	Intermediate Similarity	NPC474228
0.7971	Intermediate Similarity	NPC32285
0.7952	Intermediate Similarity	NPC184663
0.7952	Intermediate Similarity	NPC469546
0.7945	Intermediate Similarity	NPC307176
0.791	Intermediate Similarity	NPC311852
0.7867	Intermediate Similarity	NPC309852
0.7857	Intermediate Similarity	NPC469662
0.7857	Intermediate Similarity	NPC6697
0.7838	Intermediate Similarity	NPC190035
0.7826	Intermediate Similarity	NPC60565
0.7826	Intermediate Similarity	NPC213152
0.7778	Intermediate Similarity	NPC470812
0.7765	Intermediate Similarity	NPC230064
0.7763	Intermediate Similarity	NPC65650
0.7763	Intermediate Similarity	NPC476346
0.7761	Intermediate Similarity	NPC115385
0.7746	Intermediate Similarity	NPC268039
0.7733	Intermediate Similarity	NPC130016
0.7733	Intermediate Similarity	NPC470045
0.7733	Intermediate Similarity	NPC109576
0.7733	Intermediate Similarity	NPC474488
0.7733	Intermediate Similarity	NPC470044
0.7733	Intermediate Similarity	NPC251705
0.7733	Intermediate Similarity	NPC56747
0.7733	Intermediate Similarity	NPC180015
0.7714	Intermediate Similarity	NPC202118
0.7714	Intermediate Similarity	NPC197238
0.7714	Intermediate Similarity	NPC165695
0.7703	Intermediate Similarity	NPC35734
0.7703	Intermediate Similarity	NPC151045
0.7703	Intermediate Similarity	NPC159577
0.7703	Intermediate Similarity	NPC246722
0.7703	Intermediate Similarity	NPC282593
0.7692	Intermediate Similarity	NPC253561
0.7692	Intermediate Similarity	NPC80088
0.7692	Intermediate Similarity	NPC62336
0.7683	Intermediate Similarity	NPC70685
0.7662	Intermediate Similarity	NPC470525
0.7662	Intermediate Similarity	NPC69408
0.7662	Intermediate Similarity	NPC263582
0.7662	Intermediate Similarity	NPC1254
0.7654	Intermediate Similarity	NPC41539
0.7654	Intermediate Similarity	NPC307258
0.7654	Intermediate Similarity	NPC470165
0.7647	Intermediate Similarity	NPC170799
0.7647	Intermediate Similarity	NPC308108
0.7632	Intermediate Similarity	NPC20025
0.7632	Intermediate Similarity	NPC255021
0.7632	Intermediate Similarity	NPC474797
0.7632	Intermediate Similarity	NPC329866
0.7632	Intermediate Similarity	NPC474796
0.7625	Intermediate Similarity	NPC90055
0.7625	Intermediate Similarity	NPC116797
0.7625	Intermediate Similarity	NPC149237
0.7606	Intermediate Similarity	NPC473902
0.76	Intermediate Similarity	NPC5701
0.76	Intermediate Similarity	NPC305501
0.76	Intermediate Similarity	NPC115023
0.76	Intermediate Similarity	NPC223187
0.76	Intermediate Similarity	NPC234707
0.76	Intermediate Similarity	NPC21944
0.76	Intermediate Similarity	NPC225467
0.7595	Intermediate Similarity	NPC152061
0.7595	Intermediate Similarity	NPC476177
0.759	Intermediate Similarity	NPC168248
0.7576	Intermediate Similarity	NPC100809
0.7576	Intermediate Similarity	NPC250539
0.7576	Intermediate Similarity	NPC209431
0.7571	Intermediate Similarity	NPC475795
0.7571	Intermediate Similarity	NPC97322
0.7568	Intermediate Similarity	NPC286814
0.7564	Intermediate Similarity	NPC472300
0.7564	Intermediate Similarity	NPC197659
0.7532	Intermediate Similarity	NPC293803
0.7532	Intermediate Similarity	NPC473171
0.75	Intermediate Similarity	NPC2482
0.75	Intermediate Similarity	NPC471514
0.75	Intermediate Similarity	NPC193695
0.75	Intermediate Similarity	NPC192427
0.75	Intermediate Similarity	NPC472478
0.75	Intermediate Similarity	NPC472301
0.75	Intermediate Similarity	NPC144947
0.747	Intermediate Similarity	NPC33881
0.747	Intermediate Similarity	NPC472931
0.747	Intermediate Similarity	NPC472940
0.747	Intermediate Similarity	NPC2709
0.7468	Intermediate Similarity	NPC189485
0.7468	Intermediate Similarity	NPC59436
0.7463	Intermediate Similarity	NPC200258
0.7439	Intermediate Similarity	NPC118423
0.7436	Intermediate Similarity	NPC180886
0.7432	Intermediate Similarity	NPC296697
0.7432	Intermediate Similarity	NPC82477
0.7432	Intermediate Similarity	NPC20610
0.7432	Intermediate Similarity	NPC39157
0.7432	Intermediate Similarity	NPC142754
0.7424	Intermediate Similarity	NPC23117
0.7424	Intermediate Similarity	NPC268564
0.7407	Intermediate Similarity	NPC121984
0.7407	Intermediate Similarity	NPC474085
0.7407	Intermediate Similarity	NPC119229
0.7407	Intermediate Similarity	NPC99308
0.7407	Intermediate Similarity	NPC189237
0.7403	Intermediate Similarity	NPC75485
0.7403	Intermediate Similarity	NPC168975
0.7403	Intermediate Similarity	NPC159497
0.7397	Intermediate Similarity	NPC323005
0.7391	Intermediate Similarity	NPC60772
0.7375	Intermediate Similarity	NPC472490
0.7375	Intermediate Similarity	NPC27817
0.7375	Intermediate Similarity	NPC283789
0.7375	Intermediate Similarity	NPC308038
0.7368	Intermediate Similarity	NPC133253
0.7342	Intermediate Similarity	NPC325946
0.7342	Intermediate Similarity	NPC257666
0.7342	Intermediate Similarity	NPC97377
0.7342	Intermediate Similarity	NPC266193
0.7333	Intermediate Similarity	NPC182815
0.7326	Intermediate Similarity	NPC472983
0.7317	Intermediate Similarity	NPC103486
0.7317	Intermediate Similarity	NPC238991
0.7317	Intermediate Similarity	NPC142683
0.7317	Intermediate Similarity	NPC302661
0.7317	Intermediate Similarity	NPC268122
0.7313	Intermediate Similarity	NPC5626
0.7308	Intermediate Similarity	NPC255650
0.7308	Intermediate Similarity	NPC114236
0.7297	Intermediate Similarity	NPC220210
0.7297	Intermediate Similarity	NPC20181
0.7286	Intermediate Similarity	NPC96551
0.7286	Intermediate Similarity	NPC259261
0.7286	Intermediate Similarity	NPC285594
0.7284	Intermediate Similarity	NPC26139
0.7284	Intermediate Similarity	NPC108955
0.7284	Intermediate Similarity	NPC172013
0.7284	Intermediate Similarity	NPC474956
0.7284	Intermediate Similarity	NPC476809
0.7273	Intermediate Similarity	NPC22182
0.7262	Intermediate Similarity	NPC11711
0.7262	Intermediate Similarity	NPC476426
0.7262	Intermediate Similarity	NPC133652
0.7262	Intermediate Similarity	NPC8571
0.7262	Intermediate Similarity	NPC189311
0.725	Intermediate Similarity	NPC469996
0.725	Intermediate Similarity	NPC471409
0.725	Intermediate Similarity	NPC475994
0.725	Intermediate Similarity	NPC82635
0.725	Intermediate Similarity	NPC74410
0.725	Intermediate Similarity	NPC275494
0.7241	Intermediate Similarity	NPC191684
0.7237	Intermediate Similarity	NPC40574
0.7229	Intermediate Similarity	NPC64600
0.7229	Intermediate Similarity	NPC102197
0.7222	Intermediate Similarity	NPC472306

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 NPC474562 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2352
0.2-0.3	4454
0.3-0.4	1575
0.4-0.5	334
0.5-0.6	177
0.6-0.7	70
0.7-0.8	7
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
0.8194	Intermediate Similarity	NPD4691	Approved
0.8056	Intermediate Similarity	NPD4137	Phase 3
0.7945	Intermediate Similarity	NPD4747	Approved
0.7867	Intermediate Similarity	NPD4058	Approved
0.7647	Intermediate Similarity	NPD287	Approved
0.7632	Intermediate Similarity	NPD4687	Approved
0.7632	Intermediate Similarity	NPD5733	Approved
0.76	Intermediate Similarity	NPD5276	Approved
0.7432	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7073	Intermediate Similarity	NPD4695	Discontinued
0.7024	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8028	Phase 2
0.6977	Remote Similarity	NPD7146	Approved
0.6977	Remote Similarity	NPD5330	Approved
0.6977	Remote Similarity	NPD6684	Approved
0.6977	Remote Similarity	NPD7521	Approved
0.6977	Remote Similarity	NPD3618	Phase 1
0.6977	Remote Similarity	NPD6409	Approved
0.6977	Remote Similarity	NPD7334	Approved
0.6923	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD5210	Approved
0.6905	Remote Similarity	NPD4223	Phase 3
0.6905	Remote Similarity	NPD4221	Approved
0.6905	Remote Similarity	NPD3667	Approved
0.6848	Remote Similarity	NPD4697	Phase 3
0.6818	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD5737	Approved
0.6818	Remote Similarity	NPD6672	Approved
0.6818	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5690	Phase 2
0.6782	Remote Similarity	NPD5279	Phase 3
0.6778	Remote Similarity	NPD6079	Approved
0.6744	Remote Similarity	NPD4786	Approved
0.6744	Remote Similarity	NPD3668	Phase 3
0.6744	Remote Similarity	NPD4197	Approved
0.6742	Remote Similarity	NPD4753	Phase 2
0.6742	Remote Similarity	NPD5328	Approved
0.6706	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.663	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7900	Approved
0.6627	Remote Similarity	NPD3617	Approved
0.6593	Remote Similarity	NPD7515	Phase 2
0.6591	Remote Similarity	NPD4623	Approved
0.6591	Remote Similarity	NPD4690	Approved
0.6591	Remote Similarity	NPD4688	Approved
0.6591	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5280	Approved
0.6591	Remote Similarity	NPD4694	Approved
0.6591	Remote Similarity	NPD5205	Approved
0.6591	Remote Similarity	NPD4693	Phase 3
0.6591	Remote Similarity	NPD4519	Discontinued
0.6591	Remote Similarity	NPD4689	Approved
0.6591	Remote Similarity	NPD4138	Approved
0.6526	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6489	Remote Similarity	NPD5222	Approved
0.6489	Remote Similarity	NPD7732	Phase 3
0.6489	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5221	Approved
0.6452	Remote Similarity	NPD7748	Approved
0.6444	Remote Similarity	NPD5208	Approved
0.6421	Remote Similarity	NPD7902	Approved
0.6421	Remote Similarity	NPD5173	Approved
0.6383	Remote Similarity	NPD5695	Phase 3
0.6374	Remote Similarity	NPD6080	Approved
0.6374	Remote Similarity	NPD6904	Approved
0.6374	Remote Similarity	NPD6673	Approved
0.6353	Remote Similarity	NPD4195	Approved
0.6344	Remote Similarity	NPD6399	Phase 3
0.6316	Remote Similarity	NPD7614	Phase 1
0.6304	Remote Similarity	NPD5207	Approved
0.6304	Remote Similarity	NPD5692	Phase 3
0.6289	Remote Similarity	NPD5286	Approved
0.6289	Remote Similarity	NPD5285	Approved
0.6289	Remote Similarity	NPD4696	Approved
0.6282	Remote Similarity	NPD7331	Phase 2
0.6279	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD4788	Approved
0.6237	Remote Similarity	NPD5693	Phase 1
0.6237	Remote Similarity	NPD6050	Approved
0.6237	Remote Similarity	NPD5694	Approved
0.6237	Remote Similarity	NPD5284	Approved
0.6237	Remote Similarity	NPD5281	Approved
0.6224	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD6098	Approved
0.6211	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7631	Approved
0.6162	Remote Similarity	NPD5211	Phase 2
0.6162	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD4633	Approved
0.6162	Remote Similarity	NPD5225	Approved
0.6162	Remote Similarity	NPD5091	Approved
0.6162	Remote Similarity	NPD5224	Approved
0.6129	Remote Similarity	NPD4096	Approved
0.6122	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD1696	Phase 3
0.6105	Remote Similarity	NPD6001	Approved
0.61	Remote Similarity	NPD5174	Approved
0.61	Remote Similarity	NPD5175	Approved
0.6082	Remote Similarity	NPD3495	Discontinued
0.6064	Remote Similarity	NPD7609	Phase 3
0.604	Remote Similarity	NPD5141	Approved
0.6027	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4692	Approved
0.6023	Remote Similarity	NPD4139	Approved
0.6	Remote Similarity	NPD5133	Approved
0.5978	Remote Similarity	NPD650	Approved
0.5949	Remote Similarity	NPD7341	Phase 2
0.5941	Remote Similarity	NPD4754	Approved
0.5922	Remote Similarity	NPD6614	Approved
0.5922	Remote Similarity	NPD5697	Approved
0.5914	Remote Similarity	NPD4518	Approved
0.5882	Remote Similarity	NPD8039	Approved
0.5876	Remote Similarity	NPD5654	Approved
0.5875	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD6011	Approved
0.5865	Remote Similarity	NPD5128	Approved
0.5865	Remote Similarity	NPD4730	Approved
0.5865	Remote Similarity	NPD4729	Approved
0.5865	Remote Similarity	NPD5168	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5849	Remote Similarity	NPD6650	Approved
0.5849	Remote Similarity	NPD6649	Approved
0.5825	Remote Similarity	NPD4768	Approved
0.5825	Remote Similarity	NPD6008	Approved
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD4767	Approved
0.5825	Remote Similarity	NPD6675	Approved
0.5814	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6013	Approved
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6373	Approved
0.5769	Remote Similarity	NPD6412	Phase 2
0.5769	Remote Similarity	NPD4193	Approved
0.5769	Remote Similarity	NPD4194	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5769	Remote Similarity	NPD4191	Approved
0.5769	Remote Similarity	NPD4192	Approved
0.5758	Remote Similarity	NPD5959	Approved
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD5169	Approved
0.5755	Remote Similarity	NPD4634	Approved
0.5755	Remote Similarity	NPD5250	Approved
0.5755	Remote Similarity	NPD5247	Approved
0.5755	Remote Similarity	NPD5135	Approved
0.5755	Remote Similarity	NPD5249	Phase 3
0.5755	Remote Similarity	NPD5251	Approved
0.5755	Remote Similarity	NPD5248	Approved
0.5755	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6883	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD5215	Approved
0.5701	Remote Similarity	NPD5217	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5701	Remote Similarity	NPD5127	Approved
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD5216	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.5698	Remote Similarity	NPD6942	Approved
0.5698	Remote Similarity	NPD7339	Approved
0.5696	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD8297	Approved
0.5644	Remote Similarity	NPD6404	Discontinued
0.5631	Remote Similarity	NPD6052	Approved
0.5625	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7645	Phase 2
0.5604	Remote Similarity	NPD5209	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