NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	281.005
LogP:	1.579
LogD:	1.208
LogS:	-3.168
# Rotatable Bonds:	1
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	6.22
Fsp3:	0.8
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:	-4.922
MDCK Permeability:	2.1536432541324757e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	59.88311767578125%
Volume Distribution (VD):	1.065
Pgp-substrate:	41.46440505981445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.763

ADMET: Excretion

Clearance (CL):	5.893
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.622
Carcinogencity:	0.936
Eye Corrosion:	0.032
Eye Irritation:	0.724
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC478089

Natural Product ID:	NPC478089
*Common Name:**	Merulin C
IUPAC Name:	(1R,6S,9R)-10-hydroxy-10-(hydroxymethyl)-2,2,6-trimethyl-7,8-dioxatricyclo[7.3.1.01,6]tridec-3-en-5-one
Synonyms:	Merulin C
Standard InCHIKey:	NELFNNHUMIOVCO-KREAIGTHSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-12(2)5-4-10(17)13(3)15(12)7-6-14(18,9-16)11(8-15)19-20-13/h4-5,11,16,18H,6-9H2,1-3H3/t11-,13-,14?,15-/m1/s1
SMILES:	C[C@@]12C(=O)C=CC([C@]13CCC([C@@H](C3)OO2)(CO)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	70691780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002517] Chamigranes

*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
NPO33551	Thai mangrove-derived fungus	Species	n.a.	n.a.	isolated from the leaves of Xylocarpus granatum	Samutsakorn Province, Thailand	2008-JUL	PMID[21954864]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	900	nM	PMID[21954864]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	90	%	PMID[21954864]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	50	%	PMID[21954864]
NPT177	Tissue	Aorta	Rattus norvegicus	FC	=	10	n.a.	PMID[21954864]

☑ 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 NPC478089 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	208
0.1-0.2	1382
0.2-0.3	4874
0.3-0.4	8996
0.4-0.5	14288
0.5-0.6	7663
0.6-0.7	4612
0.7-0.8	664
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC470184
0.8125	Intermediate Similarity	NPC196227
0.8095	Intermediate Similarity	NPC90769
0.8065	Intermediate Similarity	NPC472324
0.8058	Intermediate Similarity	NPC293850
0.8041	Intermediate Similarity	NPC474602
0.8	Intermediate Similarity	NPC146945
0.8	Intermediate Similarity	NPC171888
0.8	Intermediate Similarity	NPC473099
0.7979	Intermediate Similarity	NPC158778
0.7917	Intermediate Similarity	NPC116726
0.7917	Intermediate Similarity	NPC99380
0.7905	Intermediate Similarity	NPC235077
0.79	Intermediate Similarity	NPC472972
0.79	Intermediate Similarity	NPC144956
0.7895	Intermediate Similarity	NPC473100
0.7857	Intermediate Similarity	NPC476245
0.7857	Intermediate Similarity	NPC473170
0.7857	Intermediate Similarity	NPC200702
0.785	Intermediate Similarity	NPC208998
0.785	Intermediate Similarity	NPC198539
0.785	Intermediate Similarity	NPC49451
0.785	Intermediate Similarity	NPC7921
0.7843	Intermediate Similarity	NPC191892
0.783	Intermediate Similarity	NPC201992
0.7826	Intermediate Similarity	NPC64600
0.7818	Intermediate Similarity	NPC469488
0.7812	Intermediate Similarity	NPC472325
0.7812	Intermediate Similarity	NPC128672
0.781	Intermediate Similarity	NPC27814
0.781	Intermediate Similarity	NPC214644
0.7788	Intermediate Similarity	NPC144854
0.7788	Intermediate Similarity	NPC3316
0.7778	Intermediate Similarity	NPC473158
0.7766	Intermediate Similarity	NPC262026
0.7757	Intermediate Similarity	NPC11252
0.7757	Intermediate Similarity	NPC289312
0.7757	Intermediate Similarity	NPC474516
0.7755	Intermediate Similarity	NPC472976
0.7755	Intermediate Similarity	NPC103527
0.7755	Intermediate Similarity	NPC472977
0.7745	Intermediate Similarity	NPC478176
0.7714	Intermediate Similarity	NPC65941
0.7714	Intermediate Similarity	NPC154608
0.7714	Intermediate Similarity	NPC192813
0.7714	Intermediate Similarity	NPC277017
0.7706	Intermediate Similarity	NPC152199
0.7706	Intermediate Similarity	NPC134869
0.7706	Intermediate Similarity	NPC328374
0.7706	Intermediate Similarity	NPC40632
0.7706	Intermediate Similarity	NPC96312
0.7706	Intermediate Similarity	NPC235539
0.7706	Intermediate Similarity	NPC251236
0.77	Intermediate Similarity	NPC18509
0.77	Intermediate Similarity	NPC273269
0.7685	Intermediate Similarity	NPC51978
0.7685	Intermediate Similarity	NPC73300
0.7685	Intermediate Similarity	NPC255017
0.7685	Intermediate Similarity	NPC194100
0.7685	Intermediate Similarity	NPC108721
0.7677	Intermediate Similarity	NPC472824
0.7677	Intermediate Similarity	NPC272617
0.7667	Intermediate Similarity	NPC478084
0.7658	Intermediate Similarity	NPC470777
0.7653	Intermediate Similarity	NPC477436
0.7653	Intermediate Similarity	NPC477435
0.7642	Intermediate Similarity	NPC41405
0.7642	Intermediate Similarity	NPC20192
0.7636	Intermediate Similarity	NPC27999
0.7636	Intermediate Similarity	NPC287343
0.7636	Intermediate Similarity	NPC122033
0.7636	Intermediate Similarity	NPC97908
0.7636	Intermediate Similarity	NPC470854
0.7636	Intermediate Similarity	NPC477116
0.7636	Intermediate Similarity	NPC474654
0.7634	Intermediate Similarity	NPC169941
0.7634	Intermediate Similarity	NPC251475
0.7629	Intermediate Similarity	NPC134321
0.7624	Intermediate Similarity	NPC114274
0.7619	Intermediate Similarity	NPC220229
0.7619	Intermediate Similarity	NPC475060
0.7619	Intermediate Similarity	NPC83744
0.7619	Intermediate Similarity	NPC165873
0.7615	Intermediate Similarity	NPC473798
0.7615	Intermediate Similarity	NPC18547
0.7615	Intermediate Similarity	NPC474906
0.7596	Intermediate Similarity	NPC160843
0.7596	Intermediate Similarity	NPC40170
0.7593	Intermediate Similarity	NPC152117
0.7593	Intermediate Similarity	NPC234042
0.7589	Intermediate Similarity	NPC478051
0.7579	Intermediate Similarity	NPC94666
0.7579	Intermediate Similarity	NPC179591
0.7576	Intermediate Similarity	NPC245972
0.7576	Intermediate Similarity	NPC471207
0.7576	Intermediate Similarity	NPC196485
0.7576	Intermediate Similarity	NPC258674
0.757	Intermediate Similarity	NPC5284
0.757	Intermediate Similarity	NPC210005
0.7568	Intermediate Similarity	NPC297179
0.7568	Intermediate Similarity	NPC17772
0.7568	Intermediate Similarity	NPC204552
0.7568	Intermediate Similarity	NPC188667
0.7568	Intermediate Similarity	NPC251310
0.7553	Intermediate Similarity	NPC136114
0.7553	Intermediate Similarity	NPC40687
0.7551	Intermediate Similarity	NPC185936
0.7551	Intermediate Similarity	NPC168027
0.7551	Intermediate Similarity	NPC472978
0.7551	Intermediate Similarity	NPC155304
0.7547	Intermediate Similarity	NPC217201
0.7547	Intermediate Similarity	NPC272576
0.7547	Intermediate Similarity	NPC329417
0.7545	Intermediate Similarity	NPC207217
0.7526	Intermediate Similarity	NPC77263
0.7526	Intermediate Similarity	NPC250592
0.7524	Intermediate Similarity	NPC260268
0.7524	Intermediate Similarity	NPC296945
0.7524	Intermediate Similarity	NPC476027
0.7524	Intermediate Similarity	NPC166607
0.7524	Intermediate Similarity	NPC319077
0.7524	Intermediate Similarity	NPC181357
0.7524	Intermediate Similarity	NPC149047
0.7524	Intermediate Similarity	NPC50692
0.7524	Intermediate Similarity	NPC202167
0.7524	Intermediate Similarity	NPC85829
0.7524	Intermediate Similarity	NPC102352
0.7524	Intermediate Similarity	NPC152695
0.7524	Intermediate Similarity	NPC150531
0.7524	Intermediate Similarity	NPC97202
0.7524	Intermediate Similarity	NPC214264
0.7524	Intermediate Similarity	NPC48733
0.7524	Intermediate Similarity	NPC302607
0.7524	Intermediate Similarity	NPC49958
0.7524	Intermediate Similarity	NPC323834
0.7524	Intermediate Similarity	NPC171137
0.75	Intermediate Similarity	NPC41070
0.75	Intermediate Similarity	NPC471243
0.75	Intermediate Similarity	NPC477438
0.75	Intermediate Similarity	NPC475775
0.75	Intermediate Similarity	NPC247957
0.75	Intermediate Similarity	NPC249187
0.75	Intermediate Similarity	NPC476529
0.75	Intermediate Similarity	NPC474229
0.75	Intermediate Similarity	NPC275583
0.75	Intermediate Similarity	NPC270046
0.75	Intermediate Similarity	NPC279143
0.75	Intermediate Similarity	NPC477437
0.75	Intermediate Similarity	NPC298904
0.75	Intermediate Similarity	NPC264048
0.7478	Intermediate Similarity	NPC473255
0.7477	Intermediate Similarity	NPC87335
0.7477	Intermediate Similarity	NPC77089
0.7477	Intermediate Similarity	NPC11710
0.7477	Intermediate Similarity	NPC163004
0.7477	Intermediate Similarity	NPC300026
0.7477	Intermediate Similarity	NPC309433
0.7476	Intermediate Similarity	NPC112613
0.7474	Intermediate Similarity	NPC471267
0.7474	Intermediate Similarity	NPC79573
0.7455	Intermediate Similarity	NPC247069
0.7453	Intermediate Similarity	NPC43285
0.7453	Intermediate Similarity	NPC44063
0.7453	Intermediate Similarity	NPC58370
0.7453	Intermediate Similarity	NPC477916
0.7449	Intermediate Similarity	NPC136801
0.7449	Intermediate Similarity	NPC230332
0.7447	Intermediate Similarity	NPC471987
0.7434	Intermediate Similarity	NPC112038
0.7434	Intermediate Similarity	NPC107338
0.7434	Intermediate Similarity	NPC109607
0.7431	Intermediate Similarity	NPC205534
0.7431	Intermediate Similarity	NPC472002
0.7429	Intermediate Similarity	NPC209502
0.7429	Intermediate Similarity	NPC204833
0.7429	Intermediate Similarity	NPC65523
0.7429	Intermediate Similarity	NPC284865
0.7429	Intermediate Similarity	NPC475036
0.7426	Intermediate Similarity	NPC469528
0.7426	Intermediate Similarity	NPC61369
0.7426	Intermediate Similarity	NPC94337
0.7426	Intermediate Similarity	NPC5532
0.7426	Intermediate Similarity	NPC469545
0.7426	Intermediate Similarity	NPC469369
0.7419	Intermediate Similarity	NPC67254
0.7407	Intermediate Similarity	NPC5103
0.7404	Intermediate Similarity	NPC473424
0.74	Intermediate Similarity	NPC473172
0.74	Intermediate Similarity	NPC477439
0.74	Intermediate Similarity	NPC23170
0.7387	Intermediate Similarity	NPC179626
0.7383	Intermediate Similarity	NPC168883
0.7379	Intermediate Similarity	NPC474720
0.7379	Intermediate Similarity	NPC15390
0.7379	Intermediate Similarity	NPC316964
0.7374	Intermediate Similarity	NPC131872
0.7374	Intermediate Similarity	NPC473167
0.7374	Intermediate Similarity	NPC73457
0.7368	Intermediate Similarity	NPC275675
0.7368	Intermediate Similarity	NPC102822

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 NPC478089 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1834
0.2-0.3	3908
0.3-0.4	2138
0.4-0.5	673
0.5-0.6	225
0.6-0.7	102
0.7-0.8	80
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
0.7905	Intermediate Similarity	NPD4634	Approved
0.79	Intermediate Similarity	NPD5286	Approved
0.79	Intermediate Similarity	NPD5285	Approved
0.79	Intermediate Similarity	NPD4696	Approved
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD5226	Approved
0.7745	Intermediate Similarity	NPD4633	Approved
0.7745	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD5224	Approved
0.77	Intermediate Similarity	NPD4755	Approved
0.767	Intermediate Similarity	NPD5174	Approved
0.767	Intermediate Similarity	NPD5175	Approved
0.7647	Intermediate Similarity	NPD5223	Approved
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD5141	Approved
0.7549	Intermediate Similarity	NPD4700	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7523	Intermediate Similarity	NPD4632	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD6899	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD6079	Approved
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7281	Intermediate Similarity	NPD6319	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7255	Intermediate Similarity	NPD4697	Phase 3
0.7248	Intermediate Similarity	NPD7102	Approved
0.7248	Intermediate Similarity	NPD6883	Approved
0.7248	Intermediate Similarity	NPD5248	Approved
0.7248	Intermediate Similarity	NPD7290	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6011	Approved
0.7196	Intermediate Similarity	NPD4767	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7196	Intermediate Similarity	NPD4768	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7182	Intermediate Similarity	NPD5217	Approved
0.7182	Intermediate Similarity	NPD6649	Approved
0.7182	Intermediate Similarity	NPD6847	Approved
0.7182	Intermediate Similarity	NPD6869	Approved
0.7182	Intermediate Similarity	NPD6617	Approved
0.7182	Intermediate Similarity	NPD6650	Approved
0.7182	Intermediate Similarity	NPD5215	Approved
0.7182	Intermediate Similarity	NPD5216	Approved
0.7182	Intermediate Similarity	NPD8130	Phase 1
0.7172	Intermediate Similarity	NPD5328	Approved
0.717	Intermediate Similarity	NPD4754	Approved
0.7168	Intermediate Similarity	NPD6009	Approved
0.713	Intermediate Similarity	NPD6054	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7117	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5135	Approved
0.7091	Intermediate Similarity	NPD5169	Approved
0.7069	Intermediate Similarity	NPD6015	Approved
0.7069	Intermediate Similarity	NPD6016	Approved
0.7064	Intermediate Similarity	NPD7320	Approved
0.7041	Intermediate Similarity	NPD3618	Phase 1
0.7027	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD6370	Approved
0.7009	Intermediate Similarity	NPD5988	Approved
0.7	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD5210	Approved
0.699	Remote Similarity	NPD4629	Approved
0.6961	Remote Similarity	NPD4202	Approved
0.6947	Remote Similarity	NPD4695	Discontinued
0.6923	Remote Similarity	NPD5983	Phase 2
0.6909	Remote Similarity	NPD5168	Approved
0.6893	Remote Similarity	NPD5282	Discontinued
0.6891	Remote Similarity	NPD7492	Approved
0.6863	Remote Similarity	NPD7515	Phase 2
0.6842	Remote Similarity	NPD5167	Approved
0.6838	Remote Similarity	NPD6059	Approved
0.6833	Remote Similarity	NPD6616	Approved
0.6807	Remote Similarity	NPD8328	Phase 3
0.6807	Remote Similarity	NPD7604	Phase 2
0.6804	Remote Similarity	NPD3667	Approved
0.68	Remote Similarity	NPD3573	Approved
0.6783	Remote Similarity	NPD6274	Approved
0.6777	Remote Similarity	NPD7078	Approved
0.6771	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1696	Phase 3
0.6752	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD7101	Approved
0.6726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6317	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.67	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5690	Phase 2
0.67	Remote Similarity	NPD5279	Phase 3
0.6699	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.661	Remote Similarity	NPD4522	Approved
0.6581	Remote Similarity	NPD7115	Discovery
0.6581	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD7748	Approved
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7902	Approved
0.6542	Remote Similarity	NPD6084	Phase 2
0.6542	Remote Similarity	NPD6083	Phase 2
0.6509	Remote Similarity	NPD5695	Phase 3
0.6505	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6101	Approved
0.6504	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD6921	Approved
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4197	Approved
0.6496	Remote Similarity	NPD6868	Approved
0.6436	Remote Similarity	NPD5329	Approved
0.6436	Remote Similarity	NPD1694	Approved
0.6392	Remote Similarity	NPD3617	Approved
0.6373	Remote Similarity	NPD5280	Approved
0.6373	Remote Similarity	NPD4694	Approved
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6355	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3668	Phase 3
0.633	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD5778	Approved
0.6321	Remote Similarity	NPD6399	Phase 3
0.6321	Remote Similarity	NPD5779	Approved
0.632	Remote Similarity	NPD6033	Approved
0.6316	Remote Similarity	NPD6686	Approved
0.63	Remote Similarity	NPD4221	Approved
0.63	Remote Similarity	NPD4223	Phase 3
0.629	Remote Similarity	NPD7507	Approved
0.6264	Remote Similarity	NPD7331	Phase 2
0.6262	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD3703	Phase 2
0.6226	Remote Similarity	NPD5284	Approved
0.6226	Remote Similarity	NPD5281	Approved
0.6216	Remote Similarity	NPD5344	Discontinued
0.6214	Remote Similarity	NPD4623	Approved
0.6214	Remote Similarity	NPD4519	Discontinued
0.6182	Remote Similarity	NPD4225	Approved
0.6182	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD7341	Phase 2
0.6142	Remote Similarity	NPD7319	Approved
0.6132	Remote Similarity	NPD46	Approved
0.6132	Remote Similarity	NPD6698	Approved
0.6126	Remote Similarity	NPD7640	Approved
0.6126	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7525	Registered
0.61	Remote Similarity	NPD5368	Approved
0.6098	Remote Similarity	NPD8517	Approved
0.6098	Remote Similarity	NPD8513	Phase 3
0.6098	Remote Similarity	NPD8515	Approved
0.6098	Remote Similarity	NPD8516	Approved
0.6095	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD6672	Approved
0.6087	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6110	Phase 1
0.6058	Remote Similarity	NPD4690	Approved
0.6058	Remote Similarity	NPD4688	Approved
0.6058	Remote Similarity	NPD4689	Approved
0.6058	Remote Similarity	NPD4693	Phase 3
0.6058	Remote Similarity	NPD4138	Approved
0.6058	Remote Similarity	NPD5205	Approved
0.6047	Remote Similarity	NPD7260	Phase 2
0.6019	Remote Similarity	NPD5133	Approved
0.6018	Remote Similarity	NPD5091	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD7645	Phase 2
0.598	Remote Similarity	NPD6435	Approved
0.5969	Remote Similarity	NPD5956	Approved
0.5966	Remote Similarity	NPD6053	Discontinued
0.5943	Remote Similarity	NPD4518	Approved
0.5932	Remote Similarity	NPD6371	Approved
0.5926	Remote Similarity	NPD7983	Approved
0.5926	Remote Similarity	NPD5694	Approved
0.5922	Remote Similarity	NPD4788	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