NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	278.135
LogP:	1.567
LogD:	0.975
LogS:	-3.095
# Rotatable Bonds:	1
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	4.546
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678
MDCK Permeability:	5.1185896154493093e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	71.46096801757812%
Volume Distribution (VD):	0.238
Pgp-substrate:	16.841096878051758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.486
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.267
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	8.094
Half-life (T1/2):	0.672

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.396
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.091
Carcinogencity:	0.069
Eye Corrosion:	0.006
Eye Irritation:	0.077
Respiratory Toxicity:	0.282

Download Data

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

Natural Product: NPC473099

Natural Product ID:	NPC473099
*Common Name:**	UUTDDCCHVKTGBI-DNGGIMRHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UUTDDCCHVKTGBI-DNGGIMRHSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-7(2)9-6-15(4)8(3)12(17)14(19)13(18)10(15)5-11(9)16/h5,8-9,12-14,17-19H,1,6H2,2-4H3/t8-,9-,12+,13+,14+,15+/m0/s1
SMILES:	CC1C(C(C(C2=CC(=O)C(CC12C)C(=C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609682
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane 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
NPO33112	guignardia mangiferae	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26241103]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6400.0	nM	PMID[466162]

☑ 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 NPC473099 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	189
0.1-0.2	1158
0.2-0.3	4018
0.3-0.4	6707
0.4-0.5	15973
0.5-0.6	7672
0.6-0.7	5605
0.7-0.8	1308
0.8-0.85	52
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC473100
0.9205	High Similarity	NPC116726
0.9	High Similarity	NPC196227
0.8721	High Similarity	NPC169941
0.8721	High Similarity	NPC251475
0.8696	High Similarity	NPC476245
0.869	High Similarity	NPC281138
0.8636	High Similarity	NPC472985
0.8636	High Similarity	NPC472986
0.8588	High Similarity	NPC172013
0.8478	Intermediate Similarity	NPC109305
0.8471	Intermediate Similarity	NPC308038
0.8462	Intermediate Similarity	NPC134321
0.8452	Intermediate Similarity	NPC197659
0.8404	Intermediate Similarity	NPC117133
0.8404	Intermediate Similarity	NPC202833
0.8391	Intermediate Similarity	NPC93590
0.8387	Intermediate Similarity	NPC472976
0.8387	Intermediate Similarity	NPC472977
0.8384	Intermediate Similarity	NPC477916
0.8352	Intermediate Similarity	NPC314727
0.8352	Intermediate Similarity	NPC472983
0.8316	Intermediate Similarity	NPC474938
0.8316	Intermediate Similarity	NPC474785
0.8315	Intermediate Similarity	NPC15807
0.8295	Intermediate Similarity	NPC64600
0.8283	Intermediate Similarity	NPC149047
0.8265	Intermediate Similarity	NPC249187
0.8265	Intermediate Similarity	NPC247957
0.8261	Intermediate Similarity	NPC128672
0.8222	Intermediate Similarity	NPC473226
0.8222	Intermediate Similarity	NPC179591
0.8222	Intermediate Similarity	NPC472974
0.82	Intermediate Similarity	NPC83744
0.82	Intermediate Similarity	NPC220229
0.82	Intermediate Similarity	NPC475060
0.8191	Intermediate Similarity	NPC474690
0.8182	Intermediate Similarity	NPC209502
0.8182	Intermediate Similarity	NPC204833
0.8182	Intermediate Similarity	NPC72255
0.8172	Intermediate Similarity	NPC73457
0.8172	Intermediate Similarity	NPC472978
0.8172	Intermediate Similarity	NPC155304
0.8172	Intermediate Similarity	NPC131872
0.8172	Intermediate Similarity	NPC233116
0.8161	Intermediate Similarity	NPC104120
0.8161	Intermediate Similarity	NPC157895
0.8161	Intermediate Similarity	NPC148685
0.814	Intermediate Similarity	NPC178852
0.8132	Intermediate Similarity	NPC472324
0.8125	Intermediate Similarity	NPC320306
0.8125	Intermediate Similarity	NPC471916
0.8119	Intermediate Similarity	NPC217201
0.8119	Intermediate Similarity	NPC329417
0.8119	Intermediate Similarity	NPC65941
0.8118	Intermediate Similarity	NPC263582
0.8111	Intermediate Similarity	NPC471267
0.8105	Intermediate Similarity	NPC272617
0.8105	Intermediate Similarity	NPC473170
0.8105	Intermediate Similarity	NPC53565
0.8105	Intermediate Similarity	NPC271195
0.81	Intermediate Similarity	NPC296945
0.81	Intermediate Similarity	NPC85829
0.81	Intermediate Similarity	NPC202167
0.81	Intermediate Similarity	NPC260268
0.81	Intermediate Similarity	NPC150531
0.81	Intermediate Similarity	NPC49958
0.81	Intermediate Similarity	NPC111952
0.81	Intermediate Similarity	NPC257353
0.81	Intermediate Similarity	NPC302607
0.81	Intermediate Similarity	NPC152695
0.81	Intermediate Similarity	NPC476027
0.81	Intermediate Similarity	NPC97202
0.81	Intermediate Similarity	NPC214264
0.81	Intermediate Similarity	NPC48733
0.81	Intermediate Similarity	NPC319077
0.81	Intermediate Similarity	NPC323834
0.81	Intermediate Similarity	NPC50692
0.81	Intermediate Similarity	NPC171137
0.809	Intermediate Similarity	NPC66764
0.809	Intermediate Similarity	NPC110150
0.8077	Intermediate Similarity	NPC108721
0.8077	Intermediate Similarity	NPC73300
0.8068	Intermediate Similarity	NPC470298
0.8065	Intermediate Similarity	NPC48010
0.8061	Intermediate Similarity	NPC97435
0.8061	Intermediate Similarity	NPC207885
0.8061	Intermediate Similarity	NPC112613
0.8043	Intermediate Similarity	NPC158778
0.8043	Intermediate Similarity	NPC104560
0.8039	Intermediate Similarity	NPC11710
0.8039	Intermediate Similarity	NPC87335
0.8039	Intermediate Similarity	NPC163004
0.8023	Intermediate Similarity	NPC74995
0.8023	Intermediate Similarity	NPC266193
0.8023	Intermediate Similarity	NPC257666
0.8023	Intermediate Similarity	NPC203403
0.8021	Intermediate Similarity	NPC473158
0.802	Intermediate Similarity	NPC143609
0.802	Intermediate Similarity	NPC67321
0.802	Intermediate Similarity	NPC187435
0.8	Intermediate Similarity	NPC470958
0.8	Intermediate Similarity	NPC40687
0.8	Intermediate Similarity	NPC196485
0.8	Intermediate Similarity	NPC478089
0.8	Intermediate Similarity	NPC245972
0.8	Intermediate Similarity	NPC103527
0.8	Intermediate Similarity	NPC114236
0.8	Intermediate Similarity	NPC470957
0.7981	Intermediate Similarity	NPC472002
0.798	Intermediate Similarity	NPC473424
0.798	Intermediate Similarity	NPC478176
0.798	Intermediate Similarity	NPC477915
0.7979	Intermediate Similarity	NPC473998
0.7978	Intermediate Similarity	NPC38796
0.7978	Intermediate Similarity	NPC158411
0.7959	Intermediate Similarity	NPC154072
0.7959	Intermediate Similarity	NPC327431
0.7957	Intermediate Similarity	NPC77263
0.7957	Intermediate Similarity	NPC229871
0.7957	Intermediate Similarity	NPC31985
0.7957	Intermediate Similarity	NPC309603
0.7957	Intermediate Similarity	NPC469319
0.7957	Intermediate Similarity	NPC472973
0.7957	Intermediate Similarity	NPC1015
0.7957	Intermediate Similarity	NPC473999
0.7957	Intermediate Similarity	NPC250592
0.7955	Intermediate Similarity	NPC471514
0.7941	Intermediate Similarity	NPC306265
0.7938	Intermediate Similarity	NPC135685
0.7938	Intermediate Similarity	NPC470522
0.7931	Intermediate Similarity	NPC475994
0.7931	Intermediate Similarity	NPC62336
0.7921	Intermediate Similarity	NPC166607
0.7917	Intermediate Similarity	NPC180950
0.7917	Intermediate Similarity	NPC266899
0.7917	Intermediate Similarity	NPC200702
0.7912	Intermediate Similarity	NPC79573
0.7907	Intermediate Similarity	NPC472305
0.79	Intermediate Similarity	NPC478057
0.79	Intermediate Similarity	NPC95899
0.79	Intermediate Similarity	NPC475050
0.79	Intermediate Similarity	NPC99266
0.7895	Intermediate Similarity	NPC69454
0.7895	Intermediate Similarity	NPC472930
0.7895	Intermediate Similarity	NPC474736
0.7889	Intermediate Similarity	NPC297398
0.7889	Intermediate Similarity	NPC105173
0.7889	Intermediate Similarity	NPC471987
0.7885	Intermediate Similarity	NPC188738
0.7882	Intermediate Similarity	NPC470299
0.7879	Intermediate Similarity	NPC256247
0.7872	Intermediate Similarity	NPC230332
0.7872	Intermediate Similarity	NPC472325
0.7865	Intermediate Similarity	NPC473420
0.7865	Intermediate Similarity	NPC471270
0.7865	Intermediate Similarity	NPC226068
0.7864	Intermediate Similarity	NPC214644
0.7857	Intermediate Similarity	NPC478056
0.7857	Intermediate Similarity	NPC216478
0.7857	Intermediate Similarity	NPC103051
0.7849	Intermediate Similarity	NPC473229
0.7849	Intermediate Similarity	NPC471722
0.7843	Intermediate Similarity	NPC230541
0.7841	Intermediate Similarity	NPC152061
0.7835	Intermediate Similarity	NPC134072
0.7835	Intermediate Similarity	NPC19376
0.7835	Intermediate Similarity	NPC249954
0.7835	Intermediate Similarity	NPC25848
0.7835	Intermediate Similarity	NPC234993
0.7835	Intermediate Similarity	NPC307282
0.7835	Intermediate Similarity	NPC305464
0.7835	Intermediate Similarity	NPC94337
0.7826	Intermediate Similarity	NPC262026
0.7826	Intermediate Similarity	NPC194417
0.7826	Intermediate Similarity	NPC198761
0.7826	Intermediate Similarity	NPC475069
0.7826	Intermediate Similarity	NPC94666
0.7826	Intermediate Similarity	NPC470955
0.7826	Intermediate Similarity	NPC175145
0.7826	Intermediate Similarity	NPC82979
0.7822	Intermediate Similarity	NPC160843
0.7816	Intermediate Similarity	NPC34110
0.7812	Intermediate Similarity	NPC8993
0.7812	Intermediate Similarity	NPC111015
0.7812	Intermediate Similarity	NPC159365
0.7812	Intermediate Similarity	NPC87095
0.7812	Intermediate Similarity	NPC299100
0.781	Intermediate Similarity	NPC207251
0.7802	Intermediate Similarity	NPC130966
0.78	Intermediate Similarity	NPC234892
0.78	Intermediate Similarity	NPC476081
0.78	Intermediate Similarity	NPC137430
0.78	Intermediate Similarity	NPC293753
0.78	Intermediate Similarity	NPC295791
0.7789	Intermediate Similarity	NPC475441
0.7789	Intermediate Similarity	NPC63748
0.7789	Intermediate Similarity	NPC473944
0.7789	Intermediate Similarity	NPC475806
0.7788	Intermediate Similarity	NPC76084

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 NPC473099 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1586
0.2-0.3	3633
0.3-0.4	2422
0.4-0.5	888
0.5-0.6	237
0.6-0.7	203
0.7-0.8	9
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
0.7826	Intermediate Similarity	NPD3618	Phase 1
0.7604	Intermediate Similarity	NPD7515	Phase 2
0.7582	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD5328	Approved
0.7451	Intermediate Similarity	NPD5211	Phase 2
0.7423	Intermediate Similarity	NPD6079	Approved
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD4786	Approved
0.7419	Intermediate Similarity	NPD3666	Approved
0.74	Intermediate Similarity	NPD4755	Approved
0.7358	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4202	Approved
0.7327	Intermediate Similarity	NPD4225	Approved
0.7308	Intermediate Similarity	NPD5141	Approved
0.73	Intermediate Similarity	NPD5222	Approved
0.73	Intermediate Similarity	NPD4697	Phase 3
0.73	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5221	Approved
0.729	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7255	Intermediate Similarity	NPD7640	Approved
0.7255	Intermediate Similarity	NPD7639	Approved
0.7255	Intermediate Similarity	NPD5286	Approved
0.7255	Intermediate Similarity	NPD4700	Approved
0.7255	Intermediate Similarity	NPD4696	Approved
0.7255	Intermediate Similarity	NPD5285	Approved
0.7228	Intermediate Similarity	NPD5173	Approved
0.7216	Intermediate Similarity	NPD4753	Phase 2
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7174	Intermediate Similarity	NPD4695	Discontinued
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD7638	Approved
0.7115	Intermediate Similarity	NPD5225	Approved
0.7115	Intermediate Similarity	NPD4633	Approved
0.7115	Intermediate Similarity	NPD5224	Approved
0.7115	Intermediate Similarity	NPD5226	Approved
0.7083	Intermediate Similarity	NPD5279	Phase 3
0.7083	Intermediate Similarity	NPD4623	Approved
0.7083	Intermediate Similarity	NPD4519	Discontinued
0.7059	Intermediate Similarity	NPD7902	Approved
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7048	Intermediate Similarity	NPD5175	Approved
0.7048	Intermediate Similarity	NPD5174	Approved
0.7019	Intermediate Similarity	NPD5344	Discontinued
0.7019	Intermediate Similarity	NPD5223	Approved
0.701	Intermediate Similarity	NPD7524	Approved
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.6989	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1694	Approved
0.6979	Remote Similarity	NPD1696	Phase 3
0.6972	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4632	Approved
0.6916	Remote Similarity	NPD7128	Approved
0.6916	Remote Similarity	NPD4767	Approved
0.6916	Remote Similarity	NPD4768	Approved
0.6916	Remote Similarity	NPD5739	Approved
0.6916	Remote Similarity	NPD6675	Approved
0.6916	Remote Similarity	NPD6402	Approved
0.6907	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4754	Approved
0.6882	Remote Similarity	NPD6929	Approved
0.6863	Remote Similarity	NPD4629	Approved
0.6863	Remote Similarity	NPD5210	Approved
0.6852	Remote Similarity	NPD5697	Approved
0.6852	Remote Similarity	NPD5701	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6842	Remote Similarity	NPD4221	Approved
0.6832	Remote Similarity	NPD6399	Phase 3
0.6809	Remote Similarity	NPD6930	Phase 2
0.6809	Remote Similarity	NPD6931	Approved
0.68	Remote Similarity	NPD6698	Approved
0.68	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD4729	Approved
0.6789	Remote Similarity	NPD4730	Approved
0.6789	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD5128	Approved
0.6789	Remote Similarity	NPD7320	Approved
0.6789	Remote Similarity	NPD6899	Approved
0.6789	Remote Similarity	NPD6686	Approved
0.6771	Remote Similarity	NPD6110	Phase 1
0.6771	Remote Similarity	NPD6695	Phase 3
0.6765	Remote Similarity	NPD7900	Approved
0.6765	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD6084	Phase 2
0.6731	Remote Similarity	NPD6083	Phase 2
0.6727	Remote Similarity	NPD6373	Approved
0.6727	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6372	Approved
0.6727	Remote Similarity	NPD6013	Approved
0.6727	Remote Similarity	NPD6012	Approved
0.6727	Remote Similarity	NPD6014	Approved
0.6724	Remote Similarity	NPD6319	Approved
0.6702	Remote Similarity	NPD7645	Phase 2
0.6701	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4197	Approved
0.6699	Remote Similarity	NPD5695	Phase 3
0.6697	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD6011	Approved
0.6633	Remote Similarity	NPD5329	Approved
0.6632	Remote Similarity	NPD7514	Phase 3
0.6632	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD8264	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD5215	Approved
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD5217	Approved
0.6607	Remote Similarity	NPD5216	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD6649	Approved
0.6606	Remote Similarity	NPD6008	Approved
0.6604	Remote Similarity	NPD6648	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.6596	Remote Similarity	NPD3617	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7145	Approved
0.6581	Remote Similarity	NPD6059	Approved
0.6581	Remote Similarity	NPD6054	Approved
0.6566	Remote Similarity	NPD6409	Approved
0.6566	Remote Similarity	NPD6684	Approved
0.6566	Remote Similarity	NPD5330	Approved
0.6566	Remote Similarity	NPD7521	Approved
0.6566	Remote Similarity	NPD4138	Approved
0.6566	Remote Similarity	NPD4688	Approved
0.6566	Remote Similarity	NPD5280	Approved
0.6566	Remote Similarity	NPD7146	Approved
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4694	Approved
0.6566	Remote Similarity	NPD4689	Approved
0.6566	Remote Similarity	NPD7334	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6562	Remote Similarity	NPD6902	Approved
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8328	Phase 3
0.6549	Remote Similarity	NPD6882	Approved
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6535	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6015	Approved
0.6525	Remote Similarity	NPD6016	Approved
0.6518	Remote Similarity	NPD5135	Approved
0.6518	Remote Similarity	NPD6371	Approved
0.6518	Remote Similarity	NPD5169	Approved
0.6518	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD3573	Approved
0.65	Remote Similarity	NPD7750	Discontinued
0.6495	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD5785	Approved
0.6465	Remote Similarity	NPD6893	Approved
0.6465	Remote Similarity	NPD5363	Approved
0.6465	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7525	Registered
0.6452	Remote Similarity	NPD7339	Approved
0.6452	Remote Similarity	NPD6942	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6436	Remote Similarity	NPD6672	Approved
0.6436	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6903	Approved
0.6423	Remote Similarity	NPD7319	Approved
0.6408	Remote Similarity	NPD7983	Approved
0.6408	Remote Similarity	NPD5284	Approved
0.6408	Remote Similarity	NPD5281	Approved
0.6395	Remote Similarity	NPD368	Approved
0.6392	Remote Similarity	NPD6898	Phase 1
0.6387	Remote Similarity	NPD5983	Phase 2
0.6383	Remote Similarity	NPD6933	Approved
0.6381	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6356	Remote Similarity	NPD4522	Approved
0.6356	Remote Similarity	NPD7516	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