NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	286.691
LogP:	2.583
LogD:	2.32
LogS:	-2.744
# Rotatable Bonds:	4
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	4.363
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672
MDCK Permeability:	6.006918192724697e-05
Pgp-inhibitor:	0.159
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858
Plasma Protein Binding (PPB):	90.16114044189453%
Volume Distribution (VD):	1.217
Pgp-substrate:	14.37378215789795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.192
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.142
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	9.294
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.724
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.058
Carcinogencity:	0.679
Eye Corrosion:	0.015
Eye Irritation:	0.186
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC262026

Natural Product ID:	NPC262026
*Common Name:**	(2R,3S,4R,6R)-2,3,4-Trihydroxy-3-Methyl-6-(6-Methylhepta-1,5-Dien-2-Yl)Cyclohexanone
IUPAC Name:	(2R,3S,4R,6R)-2,3,4-trihydroxy-3-methyl-6-(6-methylhepta-1,5-dien-2-yl)cyclohexan-1-one
Synonyms:
Standard InCHIKey:	QDYJJDBZEHVSMQ-UXOAXIEHSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-9(2)6-5-7-10(3)11-8-12(16)15(4,19)14(18)13(11)17/h6,11-12,14,16,18-19H,3,5,7-8H2,1-2,4H3/t11-,12-,14+,15+/m1/s1
SMILES:	CC(=CCCC(=C)[C@H]1C[C@@H](O)[C@]([C@H](C1=O)O)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455885
PubChem CID:	11207911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724005]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724008]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099218]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332861]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387518]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16568716]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7649881]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8002401]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9711252]

☑ 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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT277	Individual Protein	Caspase-1	Homo sapiens	MIC50	=	30000.0	nM	PMID[487499]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	MIC50	=	300.0	nM	PMID[487499]

☑ 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 NPC262026 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	184
0.1-0.2	1379
0.2-0.3	5102
0.3-0.4	9336
0.4-0.5	15284
0.5-0.6	7774
0.6-0.7	3461
0.7-0.8	172
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8675	High Similarity	NPC67254
0.8372	Intermediate Similarity	NPC136114
0.8085	Intermediate Similarity	NPC236176
0.7979	Intermediate Similarity	NPC279722
0.7872	Intermediate Similarity	NPC272617
0.7865	Intermediate Similarity	NPC79573
0.7857	Intermediate Similarity	NPC191892
0.7826	Intermediate Similarity	NPC473099
0.7766	Intermediate Similarity	NPC258674
0.7766	Intermediate Similarity	NPC196227
0.7766	Intermediate Similarity	NPC103527
0.7766	Intermediate Similarity	NPC478089
0.7755	Intermediate Similarity	NPC478176
0.7742	Intermediate Similarity	NPC116726
0.7717	Intermediate Similarity	NPC473100
0.7692	Intermediate Similarity	NPC477266
0.7684	Intermediate Similarity	NPC476245
0.7677	Intermediate Similarity	NPC117185
0.767	Intermediate Similarity	NPC146945
0.767	Intermediate Similarity	NPC171888
0.7667	Intermediate Similarity	NPC187529
0.7653	Intermediate Similarity	NPC84042
0.7653	Intermediate Similarity	NPC305085
0.764	Intermediate Similarity	NPC64600
0.7634	Intermediate Similarity	NPC469464
0.7624	Intermediate Similarity	NPC165873
0.76	Intermediate Similarity	NPC284865
0.7547	Intermediate Similarity	NPC207217
0.7526	Intermediate Similarity	NPC170978
0.7525	Intermediate Similarity	NPC166607
0.7524	Intermediate Similarity	NPC208998
0.7524	Intermediate Similarity	NPC7921
0.75	Intermediate Similarity	NPC476023
0.75	Intermediate Similarity	NPC41070
0.75	Intermediate Similarity	NPC298904
0.7477	Intermediate Similarity	NPC470854
0.7477	Intermediate Similarity	NPC474654
0.7477	Intermediate Similarity	NPC287343
0.7477	Intermediate Similarity	NPC97908
0.7477	Intermediate Similarity	NPC122033
0.7476	Intermediate Similarity	NPC163004
0.7475	Intermediate Similarity	NPC112613
0.7451	Intermediate Similarity	NPC477916
0.7449	Intermediate Similarity	NPC191565
0.7447	Intermediate Similarity	NPC134321
0.7447	Intermediate Similarity	NPC128672
0.7426	Intermediate Similarity	NPC160843
0.7426	Intermediate Similarity	NPC475036
0.7423	Intermediate Similarity	NPC49371
0.7423	Intermediate Similarity	NPC21302
0.7423	Intermediate Similarity	NPC11396
0.7419	Intermediate Similarity	NPC471941
0.7412	Intermediate Similarity	NPC476649
0.7407	Intermediate Similarity	NPC251310
0.7407	Intermediate Similarity	NPC17772
0.7404	Intermediate Similarity	NPC235077
0.74	Intermediate Similarity	NPC39996
0.7391	Intermediate Similarity	NPC179591
0.7391	Intermediate Similarity	NPC475753
0.7379	Intermediate Similarity	NPC29827
0.7374	Intermediate Similarity	NPC291785
0.7374	Intermediate Similarity	NPC127408
0.7368	Intermediate Similarity	NPC230623
0.7358	Intermediate Similarity	NPC73300
0.7358	Intermediate Similarity	NPC198539
0.7358	Intermediate Similarity	NPC49451
0.7358	Intermediate Similarity	NPC108721
0.7347	Intermediate Similarity	NPC273269
0.7347	Intermediate Similarity	NPC134454
0.7347	Intermediate Similarity	NPC17326
0.7333	Intermediate Similarity	NPC474229
0.732	Intermediate Similarity	NPC473170
0.7315	Intermediate Similarity	NPC470775
0.7315	Intermediate Similarity	NPC176513
0.7312	Intermediate Similarity	NPC472324
0.7308	Intermediate Similarity	NPC87335
0.7303	Intermediate Similarity	NPC470947
0.7303	Intermediate Similarity	NPC470946
0.7303	Intermediate Similarity	NPC470945
0.7303	Intermediate Similarity	NPC472948
0.73	Intermediate Similarity	NPC207885
0.73	Intermediate Similarity	NPC256247
0.73	Intermediate Similarity	NPC118964
0.7292	Intermediate Similarity	NPC61275
0.729	Intermediate Similarity	NPC80650
0.729	Intermediate Similarity	NPC117712
0.7282	Intermediate Similarity	NPC474716
0.7282	Intermediate Similarity	NPC144854
0.7282	Intermediate Similarity	NPC83744
0.7282	Intermediate Similarity	NPC3316
0.7282	Intermediate Similarity	NPC58370
0.7282	Intermediate Similarity	NPC43285
0.7273	Intermediate Similarity	NPC212465
0.7273	Intermediate Similarity	NPC178852
0.7273	Intermediate Similarity	NPC177232
0.7264	Intermediate Similarity	NPC474516
0.7264	Intermediate Similarity	NPC280782
0.7263	Intermediate Similarity	NPC136801
0.7263	Intermediate Similarity	NPC477684
0.7263	Intermediate Similarity	NPC46758
0.7255	Intermediate Similarity	NPC209502
0.7255	Intermediate Similarity	NPC204833
0.7255	Intermediate Similarity	NPC474281
0.7253	Intermediate Similarity	NPC477785
0.7253	Intermediate Similarity	NPC477786
0.7253	Intermediate Similarity	NPC477784
0.7248	Intermediate Similarity	NPC470776
0.7248	Intermediate Similarity	NPC204552
0.7248	Intermediate Similarity	NPC188667
0.7245	Intermediate Similarity	NPC260223
0.7245	Intermediate Similarity	NPC94337
0.7241	Intermediate Similarity	NPC78935
0.7238	Intermediate Similarity	NPC100908
0.7234	Intermediate Similarity	NPC476706
0.7234	Intermediate Similarity	NPC158778
0.7234	Intermediate Similarity	NPC476707
0.7222	Intermediate Similarity	NPC328374
0.7222	Intermediate Similarity	NPC251236
0.7222	Intermediate Similarity	NPC40632
0.7222	Intermediate Similarity	NPC96312
0.7222	Intermediate Similarity	NPC179626
0.7216	Intermediate Similarity	NPC129004
0.7216	Intermediate Similarity	NPC104371
0.7216	Intermediate Similarity	NPC298919
0.7216	Intermediate Similarity	NPC111524
0.7216	Intermediate Similarity	NPC101233
0.7216	Intermediate Similarity	NPC29247
0.7216	Intermediate Similarity	NPC91772
0.7216	Intermediate Similarity	NPC289539
0.7216	Intermediate Similarity	NPC261333
0.7216	Intermediate Similarity	NPC215271
0.7216	Intermediate Similarity	NPC292374
0.7216	Intermediate Similarity	NPC153775
0.7212	Intermediate Similarity	NPC192813
0.7212	Intermediate Similarity	NPC289702
0.7212	Intermediate Similarity	NPC293850
0.7212	Intermediate Similarity	NPC154608
0.7212	Intermediate Similarity	NPC329417
0.7212	Intermediate Similarity	NPC208461
0.7212	Intermediate Similarity	NPC277017
0.7207	Intermediate Similarity	NPC102822
0.7207	Intermediate Similarity	NPC477046
0.7204	Intermediate Similarity	NPC476043
0.72	Intermediate Similarity	NPC156324
0.72	Intermediate Similarity	NPC35239
0.72	Intermediate Similarity	NPC55503
0.72	Intermediate Similarity	NPC472972
0.72	Intermediate Similarity	NPC469551
0.72	Intermediate Similarity	NPC46761
0.72	Intermediate Similarity	NPC110149
0.72	Intermediate Similarity	NPC477655
0.7188	Intermediate Similarity	NPC185936
0.7188	Intermediate Similarity	NPC168027
0.7188	Intermediate Similarity	NPC142838
0.7188	Intermediate Similarity	NPC146852
0.7184	Intermediate Similarity	NPC202167
0.7184	Intermediate Similarity	NPC85829
0.7184	Intermediate Similarity	NPC171137
0.7184	Intermediate Similarity	NPC150531
0.7184	Intermediate Similarity	NPC48733
0.7184	Intermediate Similarity	NPC49958
0.7184	Intermediate Similarity	NPC97202
0.7184	Intermediate Similarity	NPC214264
0.7184	Intermediate Similarity	NPC260268
0.7184	Intermediate Similarity	NPC319077
0.7184	Intermediate Similarity	NPC302607
0.7184	Intermediate Similarity	NPC296945
0.7184	Intermediate Similarity	NPC149047
0.7184	Intermediate Similarity	NPC50692
0.7184	Intermediate Similarity	NPC152695
0.7184	Intermediate Similarity	NPC476027
0.7182	Intermediate Similarity	NPC470777
0.7172	Intermediate Similarity	NPC473574
0.7172	Intermediate Similarity	NPC190080
0.7172	Intermediate Similarity	NPC261935
0.7172	Intermediate Similarity	NPC18509
0.7172	Intermediate Similarity	NPC272451
0.7172	Intermediate Similarity	NPC27105
0.7172	Intermediate Similarity	NPC20078
0.7172	Intermediate Similarity	NPC111187
0.7172	Intermediate Similarity	NPC106112
0.7172	Intermediate Similarity	NPC471916
0.717	Intermediate Similarity	NPC157476
0.717	Intermediate Similarity	NPC471243
0.7159	Intermediate Similarity	NPC197659
0.7158	Intermediate Similarity	NPC69627
0.7157	Intermediate Similarity	NPC312900
0.7157	Intermediate Similarity	NPC247957
0.7157	Intermediate Similarity	NPC249187
0.7157	Intermediate Similarity	NPC320294
0.7143	Intermediate Similarity	NPC312833
0.7143	Intermediate Similarity	NPC472485
0.7143	Intermediate Similarity	NPC310546
0.7143	Intermediate Similarity	NPC470257
0.7143	Intermediate Similarity	NPC200702
0.7143	Intermediate Similarity	NPC141350
0.7143	Intermediate Similarity	NPC214644
0.7143	Intermediate Similarity	NPC48362
0.7143	Intermediate Similarity	NPC266899
0.7143	Intermediate Similarity	NPC42662

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 NPC262026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1969
0.2-0.3	3908
0.3-0.4	2043
0.4-0.5	675
0.5-0.6	270
0.6-0.7	115
0.7-0.8	1
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
0.7404	Intermediate Similarity	NPD4634	Approved
0.7212	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD4697	Phase 3
0.703	Intermediate Similarity	NPD5285	Approved
0.703	Intermediate Similarity	NPD4696	Approved
0.703	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD4700	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5221	Approved
0.6893	Remote Similarity	NPD5226	Approved
0.6893	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD5225	Approved
0.6893	Remote Similarity	NPD4633	Approved
0.6893	Remote Similarity	NPD5224	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6842	Remote Similarity	NPD3618	Phase 1
0.6832	Remote Similarity	NPD5173	Approved
0.6827	Remote Similarity	NPD5175	Approved
0.6827	Remote Similarity	NPD5174	Approved
0.6814	Remote Similarity	NPD6319	Approved
0.6804	Remote Similarity	NPD5328	Approved
0.6796	Remote Similarity	NPD5223	Approved
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5778	Approved
0.6762	Remote Similarity	NPD5141	Approved
0.6727	Remote Similarity	NPD4632	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD4767	Approved
0.6698	Remote Similarity	NPD4768	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6638	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6101	Approved
0.6633	Remote Similarity	NPD4753	Phase 2
0.6609	Remote Similarity	NPD6015	Approved
0.6609	Remote Similarity	NPD6016	Approved
0.6596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3667	Approved
0.6588	Remote Similarity	NPD7331	Phase 2
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD5128	Approved
0.6574	Remote Similarity	NPD4730	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6574	Remote Similarity	NPD4729	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6552	Remote Similarity	NPD5988	Approved
0.6552	Remote Similarity	NPD6370	Approved
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD6649	Approved
0.6526	Remote Similarity	NPD6110	Phase 1
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5369	Approved
0.6486	Remote Similarity	NPD8297	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD7341	Phase 2
0.6471	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD6921	Approved
0.6458	Remote Similarity	NPD4786	Approved
0.6455	Remote Similarity	NPD5248	Approved
0.6455	Remote Similarity	NPD5251	Approved
0.6455	Remote Similarity	NPD5249	Phase 3
0.6455	Remote Similarity	NPD7290	Approved
0.6455	Remote Similarity	NPD5250	Approved
0.6455	Remote Similarity	NPD5247	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6455	Remote Similarity	NPD6883	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6436	Remote Similarity	NPD4202	Approved
0.6422	Remote Similarity	NPD6011	Approved
0.6404	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6009	Approved
0.6396	Remote Similarity	NPD5215	Approved
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD5217	Approved
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6396	Remote Similarity	NPD5216	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6383	Remote Similarity	NPD5368	Approved
0.6339	Remote Similarity	NPD6882	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD7078	Approved
0.6327	Remote Similarity	NPD5279	Phase 3
0.6327	Remote Similarity	NPD5786	Approved
0.6311	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5135	Approved
0.6306	Remote Similarity	NPD5169	Approved
0.6289	Remote Similarity	NPD3133	Approved
0.6289	Remote Similarity	NPD3665	Phase 1
0.6289	Remote Similarity	NPD3666	Approved
0.6286	Remote Similarity	NPD4225	Approved
0.6281	Remote Similarity	NPD7736	Approved
0.6273	Remote Similarity	NPD5168	Approved
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD5127	Approved
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6698	Approved
0.6238	Remote Similarity	NPD46	Approved
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7748	Approved
0.6211	Remote Similarity	NPD4695	Discontinued
0.6211	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD8513	Phase 3
0.6186	Remote Similarity	NPD8515	Approved
0.6186	Remote Similarity	NPD8517	Approved
0.6186	Remote Similarity	NPD8516	Approved
0.6186	Remote Similarity	NPD5983	Phase 2
0.6182	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6274	Approved
0.6168	Remote Similarity	NPD5344	Discontinued
0.6163	Remote Similarity	NPD3197	Phase 1
0.6154	Remote Similarity	NPD4522	Approved
0.6154	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD6033	Approved
0.6132	Remote Similarity	NPD5696	Approved
0.6122	Remote Similarity	NPD4197	Approved
0.6122	Remote Similarity	NPD3668	Phase 3
0.6117	Remote Similarity	NPD6399	Phase 3
0.61	Remote Similarity	NPD7524	Approved
0.6098	Remote Similarity	NPD7319	Approved
0.6091	Remote Similarity	NPD6008	Approved
0.6087	Remote Similarity	NPD5167	Approved
0.6083	Remote Similarity	NPD7604	Phase 2
0.6061	Remote Similarity	NPD5363	Approved
0.6061	Remote Similarity	NPD1696	Phase 3
0.6061	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5329	Approved
0.6042	Remote Similarity	NPD7525	Registered
0.6042	Remote Similarity	NPD4252	Approved
0.6036	Remote Similarity	NPD6412	Phase 2
0.6022	Remote Similarity	NPD3703	Phase 2
0.6019	Remote Similarity	NPD1700	Approved
0.6018	Remote Similarity	NPD6371	Approved
0.6018	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7100	Approved
0.6017	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD4694	Approved
0.6	Remote Similarity	NPD5280	Approved
0.6	Remote Similarity	NPD5690	Phase 2
0.5984	Remote Similarity	NPD6336	Discontinued
0.5983	Remote Similarity	NPD6317	Approved
0.5981	Remote Similarity	NPD7638	Approved
0.5977	Remote Similarity	NPD371	Approved
0.5965	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3573	Approved
0.5938	Remote Similarity	NPD7645	Phase 2
0.5935	Remote Similarity	NPD8074	Phase 3
0.5932	Remote Similarity	NPD6335	Approved
0.5932	Remote Similarity	NPD6314	Approved
0.5932	Remote Similarity	NPD6313	Approved
0.593	Remote Similarity	NPD368	Approved
0.5926	Remote Similarity	NPD7640	Approved
0.5926	Remote Similarity	NPD7639	Approved
0.5922	Remote Similarity	NPD3168	Discontinued
0.5918	Remote Similarity	NPD4223	Phase 3
0.5918	Remote Similarity	NPD4221	Approved
0.5917	Remote Similarity	NPD6909	Approved
0.5917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6908	Approved
0.5905	Remote Similarity	NPD7900	Approved
0.5905	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.59	Remote Similarity	NPD1694	Approved
0.59	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6868	Approved
0.5876	Remote Similarity	NPD6931	Approved
0.5876	Remote Similarity	NPD6930	Phase 2
0.5865	Remote Similarity	NPD7637	Suspended
0.5862	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8415	Approved
0.5859	Remote Similarity	NPD7154	Phase 3
0.5859	Remote Similarity	NPD6695	Phase 3
0.5854	Remote Similarity	NPD7507	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