NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.1
Volume:	220.378
LogP:	0.148
LogD:	-0.576
LogS:	-0.908
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	5.775
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.377
MDCK Permeability:	0.000228383
Pgp-inhibitor:	0.002
Pgp-substrate:	0.246
Human Intestinal Absorption (HIA):	0.29
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.549

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.7
Plasma Protein Binding (PPB):	19.43%
Volume Distribution (VD):	0.759
Pgp-substrate:	64.98%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	2.811
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.283
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.722
Skin Sensitization:	0.263
Carcinogencity:	0.298
Eye Corrosion:	0.012
Eye Irritation:	0.038
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC478112

Natural Product ID:	NPC478112
*Common Name:**	Trichocladinol G
IUPAC Name:	(1R,2S,5R,8S)-1-[(1S,2R)-1,2-dihydroxypropyl]-8-hydroxy-2-methyl-6-oxabicyclo[3.2.1]oct-3-en-7-one
Synonyms:
Standard InCHIKey:	WEOBCXUZBISNCZ-YRMXFSIDSA-N
Standard InCHI:	InChI=1S/C11H16O5/c1-5-3-4-7-9(14)11(5,10(15)16-7)8(13)6(2)12/h3-9,12-14H,1-2H3/t5-,6+,7+,8+,9+,11+/m0/s1
SMILES:	C[C@H]1C=C[C@@H]2[C@H]([C@]1(C(=O)O2)[C@@H]([C@@H](C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	76332013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO22918	Trichocladium opacum	Species	Melanommataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24354429]
NPO22918	Trichocladium opacum	Species	Melanommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	41700	nM	PMID[24354429]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	44300	nM	PMID[24354429]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	43600	nM	PMID[24354429]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	52300	nM	PMID[24354429]

☑ 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 NPC478112 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	167
0.1-0.2	1171
0.2-0.3	4824
0.3-0.4	11844
0.4-0.5	12268
0.5-0.6	7832
0.6-0.7	3902
0.7-0.8	661
0.8-0.85	22
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC278283
0.9268	High Similarity	NPC32676
0.8953	High Similarity	NPC478110
0.8421	Intermediate Similarity	NPC4620
0.8333	Intermediate Similarity	NPC220964
0.8333	Intermediate Similarity	NPC475676
0.8256	Intermediate Similarity	NPC52923
0.8229	Intermediate Similarity	NPC69171
0.8229	Intermediate Similarity	NPC474165
0.8214	Intermediate Similarity	NPC475210
0.8193	Intermediate Similarity	NPC474278
0.8163	Intermediate Similarity	NPC194620
0.8163	Intermediate Similarity	NPC326994
0.8163	Intermediate Similarity	NPC324327
0.8163	Intermediate Similarity	NPC474421
0.8163	Intermediate Similarity	NPC72813
0.8132	Intermediate Similarity	NPC9447
0.8125	Intermediate Similarity	NPC183571
0.8081	Intermediate Similarity	NPC55972
0.8081	Intermediate Similarity	NPC327286
0.8081	Intermediate Similarity	NPC169888
0.8081	Intermediate Similarity	NPC233379
0.8081	Intermediate Similarity	NPC14862
0.8081	Intermediate Similarity	NPC474664
0.8061	Intermediate Similarity	NPC16313
0.8061	Intermediate Similarity	NPC9303
0.8022	Intermediate Similarity	NPC473455
0.8	Intermediate Similarity	NPC119740
0.8	Intermediate Similarity	NPC15218
0.8	Intermediate Similarity	NPC150063
0.7959	Intermediate Similarity	NPC296950
0.7959	Intermediate Similarity	NPC203659
0.7931	Intermediate Similarity	NPC474252
0.7912	Intermediate Similarity	NPC87306
0.7889	Intermediate Similarity	NPC473248
0.7879	Intermediate Similarity	NPC475802
0.7857	Intermediate Similarity	NPC110989
0.7831	Intermediate Similarity	NPC474280
0.7826	Intermediate Similarity	NPC473619
0.7826	Intermediate Similarity	NPC474232
0.7822	Intermediate Similarity	NPC475922
0.7816	Intermediate Similarity	NPC297440
0.7802	Intermediate Similarity	NPC476803
0.7802	Intermediate Similarity	NPC473715
0.7791	Intermediate Similarity	NPC99651
0.7789	Intermediate Similarity	NPC477921
0.7778	Intermediate Similarity	NPC258532
0.7778	Intermediate Similarity	NPC146731
0.7778	Intermediate Similarity	NPC469910
0.7755	Intermediate Similarity	NPC225353
0.7753	Intermediate Similarity	NPC212363
0.7745	Intermediate Similarity	NPC161816
0.7745	Intermediate Similarity	NPC115257
0.7742	Intermediate Similarity	NPC473321
0.7738	Intermediate Similarity	NPC473948
0.7717	Intermediate Similarity	NPC473564
0.7708	Intermediate Similarity	NPC134454
0.7708	Intermediate Similarity	NPC17326
0.7684	Intermediate Similarity	NPC471142
0.7684	Intermediate Similarity	NPC214694
0.7684	Intermediate Similarity	NPC477922
0.7677	Intermediate Similarity	NPC475945
0.7677	Intermediate Similarity	NPC475871
0.7667	Intermediate Similarity	NPC155873
0.7667	Intermediate Similarity	NPC21469
0.766	Intermediate Similarity	NPC475912
0.7653	Intermediate Similarity	NPC472753
0.7647	Intermediate Similarity	NPC49392
0.7647	Intermediate Similarity	NPC42662
0.7647	Intermediate Similarity	NPC190400
0.7634	Intermediate Similarity	NPC15059
0.7629	Intermediate Similarity	NPC222303
0.7629	Intermediate Similarity	NPC471144
0.7614	Intermediate Similarity	NPC52861
0.7609	Intermediate Similarity	NPC137368
0.7609	Intermediate Similarity	NPC153570
0.7604	Intermediate Similarity	NPC21302
0.7604	Intermediate Similarity	NPC11396
0.7604	Intermediate Similarity	NPC473859
0.7604	Intermediate Similarity	NPC54731
0.7604	Intermediate Similarity	NPC306041
0.76	Intermediate Similarity	NPC472756
0.7586	Intermediate Similarity	NPC473981
0.7586	Intermediate Similarity	NPC473980
0.7579	Intermediate Similarity	NPC2003
0.7579	Intermediate Similarity	NPC25701
0.7576	Intermediate Similarity	NPC472754
0.7576	Intermediate Similarity	NPC474747
0.7573	Intermediate Similarity	NPC235014
0.7573	Intermediate Similarity	NPC5103
0.7556	Intermediate Similarity	NPC158756
0.7556	Intermediate Similarity	NPC38569
0.7556	Intermediate Similarity	NPC163615
0.7553	Intermediate Similarity	NPC30515
0.7553	Intermediate Similarity	NPC184463
0.7551	Intermediate Similarity	NPC475949
0.7549	Intermediate Similarity	NPC94377
0.7528	Intermediate Similarity	NPC89555
0.7527	Intermediate Similarity	NPC133450
0.7527	Intermediate Similarity	NPC79027
0.7526	Intermediate Similarity	NPC205143
0.7526	Intermediate Similarity	NPC70145
0.7526	Intermediate Similarity	NPC266842
0.7526	Intermediate Similarity	NPC91695
0.7526	Intermediate Similarity	NPC40812
0.75	Intermediate Similarity	NPC14961
0.75	Intermediate Similarity	NPC475659
0.75	Intermediate Similarity	NPC36954
0.75	Intermediate Similarity	NPC159533
0.75	Intermediate Similarity	NPC270013
0.75	Intermediate Similarity	NPC107476
0.7475	Intermediate Similarity	NPC469657
0.7475	Intermediate Similarity	NPC474742
0.7475	Intermediate Similarity	NPC244456
0.7475	Intermediate Similarity	NPC308824
0.7474	Intermediate Similarity	NPC295204
0.7474	Intermediate Similarity	NPC162205
0.7474	Intermediate Similarity	NPC476300
0.7474	Intermediate Similarity	NPC212486
0.7474	Intermediate Similarity	NPC179746
0.7474	Intermediate Similarity	NPC273579
0.7474	Intermediate Similarity	NPC81419
0.7474	Intermediate Similarity	NPC288240
0.7473	Intermediate Similarity	NPC470755
0.7471	Intermediate Similarity	NPC11796
0.7471	Intermediate Similarity	NPC218817
0.7471	Intermediate Similarity	NPC127526
0.7471	Intermediate Similarity	NPC475699
0.7449	Intermediate Similarity	NPC278386
0.7449	Intermediate Similarity	NPC159763
0.7449	Intermediate Similarity	NPC83895
0.7449	Intermediate Similarity	NPC216478
0.7449	Intermediate Similarity	NPC124512
0.7449	Intermediate Similarity	NPC187761
0.7447	Intermediate Similarity	NPC51004
0.7447	Intermediate Similarity	NPC475855
0.7447	Intermediate Similarity	NPC177668
0.7444	Intermediate Similarity	NPC170286
0.7444	Intermediate Similarity	NPC116543
0.7442	Intermediate Similarity	NPC68819
0.7429	Intermediate Similarity	NPC473877
0.7426	Intermediate Similarity	NPC474917
0.7426	Intermediate Similarity	NPC474741
0.7419	Intermediate Similarity	NPC476805
0.7419	Intermediate Similarity	NPC309656
0.7419	Intermediate Similarity	NPC202672
0.7419	Intermediate Similarity	NPC475819
0.7416	Intermediate Similarity	NPC24417
0.7407	Intermediate Similarity	NPC284707
0.74	Intermediate Similarity	NPC235369
0.74	Intermediate Similarity	NPC475986
0.74	Intermediate Similarity	NPC149371
0.74	Intermediate Similarity	NPC471148
0.74	Intermediate Similarity	NPC474709
0.7396	Intermediate Similarity	NPC474035
0.7396	Intermediate Similarity	NPC57405
0.7396	Intermediate Similarity	NPC303942
0.7396	Intermediate Similarity	NPC81386
0.7396	Intermediate Similarity	NPC250075
0.7386	Intermediate Similarity	NPC167881
0.7386	Intermediate Similarity	NPC86971
0.7386	Intermediate Similarity	NPC98557
0.7386	Intermediate Similarity	NPC321728
0.7379	Intermediate Similarity	NPC135015
0.7379	Intermediate Similarity	NPC475960
0.7379	Intermediate Similarity	NPC264819
0.7379	Intermediate Similarity	NPC308191
0.7379	Intermediate Similarity	NPC217921
0.7379	Intermediate Similarity	NPC48548
0.7379	Intermediate Similarity	NPC128795
0.7374	Intermediate Similarity	NPC288876
0.7368	Intermediate Similarity	NPC327760
0.7368	Intermediate Similarity	NPC472199
0.7368	Intermediate Similarity	NPC12172
0.7368	Intermediate Similarity	NPC475972
0.7368	Intermediate Similarity	NPC208886
0.7363	Intermediate Similarity	NPC476804
0.7363	Intermediate Similarity	NPC219966
0.7358	Intermediate Similarity	NPC469496
0.7358	Intermediate Similarity	NPC469463
0.7358	Intermediate Similarity	NPC469454
0.7356	Intermediate Similarity	NPC475711
0.7353	Intermediate Similarity	NPC476738
0.7353	Intermediate Similarity	NPC476740
0.7353	Intermediate Similarity	NPC179891
0.7347	Intermediate Similarity	NPC472290
0.7347	Intermediate Similarity	NPC73911
0.734	Intermediate Similarity	NPC474032
0.734	Intermediate Similarity	NPC78008
0.734	Intermediate Similarity	NPC307411
0.7333	Intermediate Similarity	NPC229825
0.7333	Intermediate Similarity	NPC475690
0.7333	Intermediate Similarity	NPC475046
0.7333	Intermediate Similarity	NPC304180
0.7333	Intermediate Similarity	NPC317107
0.7333	Intermediate Similarity	NPC474959
0.7333	Intermediate Similarity	NPC11383
0.7333	Intermediate Similarity	NPC310450
0.7333	Intermediate Similarity	NPC179798
0.7327	Intermediate Similarity	NPC474166

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 NPC478112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1698
0.2-0.3	3884
0.3-0.4	2325
0.4-0.5	722
0.5-0.6	293
0.6-0.7	59
0.7-0.8	15
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
0.7449	Intermediate Similarity	NPD4225	Approved
0.7447	Intermediate Similarity	NPD46	Approved
0.7447	Intermediate Similarity	NPD6698	Approved
0.7391	Intermediate Similarity	NPD4249	Approved
0.7368	Intermediate Similarity	NPD7983	Approved
0.732	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4250	Approved
0.7312	Intermediate Similarity	NPD4251	Approved
0.7238	Intermediate Similarity	NPD6371	Approved
0.7188	Intermediate Similarity	NPD7637	Suspended
0.7115	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5785	Approved
0.7083	Intermediate Similarity	NPD7838	Discovery
0.6939	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD4252	Approved
0.6903	Remote Similarity	NPD8513	Phase 3
0.6903	Remote Similarity	NPD8516	Approved
0.6903	Remote Similarity	NPD8517	Approved
0.6903	Remote Similarity	NPD8515	Approved
0.6889	Remote Similarity	NPD4268	Approved
0.6889	Remote Similarity	NPD4271	Approved
0.6887	Remote Similarity	NPD6686	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6852	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6774	Remote Similarity	NPD5209	Approved
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4822	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6737	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6110	Phase 1
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6635	Remote Similarity	NPD5344	Discontinued
0.661	Remote Similarity	NPD8074	Phase 3
0.6602	Remote Similarity	NPD7638	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5363	Approved
0.6562	Remote Similarity	NPD1694	Approved
0.6545	Remote Similarity	NPD2204	Approved
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6526	Remote Similarity	NPD7154	Phase 3
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1695	Approved
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6101	Approved
0.6458	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6435	Approved
0.6408	Remote Similarity	NPD7839	Suspended
0.6354	Remote Similarity	NPD5362	Discontinued
0.6337	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6421	Discontinued
0.63	Remote Similarity	NPD5370	Suspended
0.6275	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6319	Approved
0.6226	Remote Similarity	NPD6648	Approved
0.6211	Remote Similarity	NPD5368	Approved
0.6196	Remote Similarity	NPD8039	Approved
0.6195	Remote Similarity	NPD6053	Discontinued
0.6186	Remote Similarity	NPD8444	Approved
0.6186	Remote Similarity	NPD5331	Approved
0.6186	Remote Similarity	NPD5332	Approved
0.6182	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD4790	Discontinued
0.6136	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8451	Approved
0.61	Remote Similarity	NPD7524	Approved
0.6098	Remote Similarity	NPD7319	Approved
0.6083	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD7830	Approved
0.6083	Remote Similarity	NPD7829	Approved
0.6082	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8448	Approved
0.605	Remote Similarity	NPD7503	Approved
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6616	Approved
0.5984	Remote Similarity	NPD7507	Approved
0.5984	Remote Similarity	NPD8273	Phase 1
0.5983	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6054	Approved
0.5963	Remote Similarity	NPD7632	Discontinued
0.596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8328	Phase 3
0.5935	Remote Similarity	NPD7078	Approved
0.5932	Remote Similarity	NPD7327	Approved
0.5932	Remote Similarity	NPD7328	Approved
0.593	Remote Similarity	NPD368	Approved
0.5929	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8390	Approved
0.592	Remote Similarity	NPD8392	Approved
0.592	Remote Similarity	NPD8391	Approved
0.5917	Remote Similarity	NPD6015	Approved
0.5917	Remote Similarity	NPD6016	Approved
0.5917	Remote Similarity	NPD6921	Approved
0.5917	Remote Similarity	NPD8033	Approved
0.5902	Remote Similarity	NPD8341	Approved
0.5902	Remote Similarity	NPD8299	Approved
0.5902	Remote Similarity	NPD8342	Approved
0.5902	Remote Similarity	NPD8340	Approved
0.5891	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7736	Approved
0.5882	Remote Similarity	NPD7516	Approved
0.5876	Remote Similarity	NPD7514	Phase 3
0.5876	Remote Similarity	NPD7332	Phase 2
0.5873	Remote Similarity	NPD7260	Phase 2
0.5868	Remote Similarity	NPD5988	Approved
0.5868	Remote Similarity	NPD6370	Approved
0.5862	Remote Similarity	NPD8133	Approved
0.5859	Remote Similarity	NPD6695	Phase 3
0.5833	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD7145	Approved
0.5833	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD8294	Approved
0.5826	Remote Similarity	NPD1719	Phase 1
0.5816	Remote Similarity	NPD6902	Approved
0.5806	Remote Similarity	NPD4732	Discontinued
0.5806	Remote Similarity	NPD8293	Discontinued
0.5804	Remote Similarity	NPD6008	Approved
0.5795	Remote Similarity	NPD3197	Phase 1
0.5795	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD4228	Discovery
0.5785	Remote Similarity	NPD8296	Approved
0.5785	Remote Similarity	NPD8379	Approved
0.5785	Remote Similarity	NPD8380	Approved
0.5785	Remote Similarity	NPD8335	Approved
0.5785	Remote Similarity	NPD8378	Approved
0.5776	Remote Similarity	NPD8297	Approved
0.5765	Remote Similarity	NPD6109	Phase 1
0.5765	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3667	Approved
0.5752	Remote Similarity	NPD5697	Approved
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD7902	Approved
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD4634	Approved
0.573	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6932	Approved
0.5729	Remote Similarity	NPD6925	Approved
0.5729	Remote Similarity	NPD5776	Phase 2
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD7500	Approved
0.5702	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD6899	Approved
0.5701	Remote Similarity	NPD5695	Phase 3
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6649	Approved
0.5688	Remote Similarity	NPD5696	Approved
0.5684	Remote Similarity	NPD8264	Approved
0.5673	Remote Similarity	NPD6051	Approved
0.5667	Remote Similarity	NPD7641	Discontinued
0.5664	Remote Similarity	NPD6402	Approved
0.5664	Remote Similarity	NPD5048	Discontinued
0.5664	Remote Similarity	NPD6675	Approved
0.5664	Remote Similarity	NPD5739	Approved
0.5664	Remote Similarity	NPD6640	Phase 3
0.5664	Remote Similarity	NPD7128	Approved
0.5656	Remote Similarity	NPD5983	Phase 2
0.5652	Remote Similarity	NPD6012	Approved
0.5652	Remote Similarity	NPD6013	Approved
0.5652	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD6014	Approved
0.5652	Remote Similarity	NPD6372	Approved
0.5644	Remote Similarity	NPD4786	Approved
0.5631	Remote Similarity	NPD7750	Discontinued
0.5614	Remote Similarity	NPD6685	Approved
0.5614	Remote Similarity	NPD5701	Approved
0.5612	Remote Similarity	NPD6929	Approved
0.5607	Remote Similarity	NPD7748	Approved
0.5603	Remote Similarity	NPD7102	Approved
0.5603	Remote Similarity	NPD7290	Approved
0.5603	Remote Similarity	NPD6883	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