NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.1
Volume:	214.458
LogP:	0.683
LogD:	0.587
LogS:	-3.243
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	6.112
Fsp3:	0.909
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:	-4.96
MDCK Permeability:	0.000147855
Pgp-inhibitor:	0.005
Pgp-substrate:	0.295
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.705
Plasma Protein Binding (PPB):	15.96%
Volume Distribution (VD):	0.758
Pgp-substrate:	65.15%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	4.79
Half-life (T1/2):	0.656

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.13
Skin Sensitization:	0.433
Carcinogencity:	0.225
Eye Corrosion:	0.061
Eye Irritation:	0.159
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC478111

Natural Product ID:	NPC478111
*Common Name:**	Trichocladinol F
IUPAC Name:	(1R,2R,5S,6S,8S,11R)-5,11-dihydroxy-2,8-dimethyl-7,9-dioxatricyclo[6.2.1.01,6]undecan-10-one
Synonyms:
Standard InCHIKey:	JKNGNOXDYOQYER-FBJXANEASA-N
Standard InCHI:	InChI=1S/C11H16O5/c1-5-3-4-6(12)7-11(5)8(13)10(2,15-7)16-9(11)14/h5-8,12-13H,3-4H2,1-2H3/t5-,6+,7-,8+,10+,11+/m1/s1
SMILES:	C[C@@H]1CC[C@@H]([C@@H]2[C@]13[C@H]([C@@](O2)(OC3=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	76317425
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	56600	nM	PMID[24354429]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	51900	nM	PMID[24354429]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	61000	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 NPC478111 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	395
0.1-0.2	2992
0.2-0.3	8186
0.3-0.4	14325
0.4-0.5	6979
0.5-0.6	7062
0.6-0.7	2509
0.7-0.8	237
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8506	High Similarity	NPC471221
0.8462	Intermediate Similarity	NPC475785
0.8295	Intermediate Similarity	NPC221993
0.8261	Intermediate Similarity	NPC475765
0.8111	Intermediate Similarity	NPC470114
0.809	Intermediate Similarity	NPC476435
0.8046	Intermediate Similarity	NPC65133
0.8022	Intermediate Similarity	NPC475878
0.7979	Intermediate Similarity	NPC472145
0.7935	Intermediate Similarity	NPC475307
0.7912	Intermediate Similarity	NPC50443
0.7912	Intermediate Similarity	NPC18536
0.7907	Intermediate Similarity	NPC475743
0.7895	Intermediate Similarity	NPC253995
0.7895	Intermediate Similarity	NPC472144
0.7872	Intermediate Similarity	NPC116683
0.7857	Intermediate Similarity	NPC100078
0.7841	Intermediate Similarity	NPC79308
0.7841	Intermediate Similarity	NPC291310
0.7841	Intermediate Similarity	NPC18953
0.7826	Intermediate Similarity	NPC474065
0.7778	Intermediate Similarity	NPC213658
0.7778	Intermediate Similarity	NPC45833
0.7778	Intermediate Similarity	NPC110365
0.7778	Intermediate Similarity	NPC62202
0.7778	Intermediate Similarity	NPC166079
0.7727	Intermediate Similarity	NPC15091
0.7708	Intermediate Similarity	NPC211087
0.7692	Intermediate Similarity	NPC470872
0.7692	Intermediate Similarity	NPC470009
0.7684	Intermediate Similarity	NPC193785
0.7674	Intermediate Similarity	NPC474754
0.7667	Intermediate Similarity	NPC475729
0.7667	Intermediate Similarity	NPC476717
0.7667	Intermediate Similarity	NPC474215
0.7653	Intermediate Similarity	NPC470172
0.7653	Intermediate Similarity	NPC213528
0.7653	Intermediate Similarity	NPC244969
0.7653	Intermediate Similarity	NPC471254
0.7647	Intermediate Similarity	NPC307865
0.764	Intermediate Similarity	NPC477434
0.764	Intermediate Similarity	NPC473299
0.7619	Intermediate Similarity	NPC228411
0.7609	Intermediate Similarity	NPC77001
0.7609	Intermediate Similarity	NPC253618
0.7604	Intermediate Similarity	NPC471241
0.76	Intermediate Similarity	NPC306776
0.7582	Intermediate Similarity	NPC314364
0.7582	Intermediate Similarity	NPC51662
0.7576	Intermediate Similarity	NPC471253
0.7576	Intermediate Similarity	NPC473406
0.7558	Intermediate Similarity	NPC191345
0.7558	Intermediate Similarity	NPC252483
0.7556	Intermediate Similarity	NPC476715
0.7556	Intermediate Similarity	NPC473350
0.7553	Intermediate Similarity	NPC182740
0.7553	Intermediate Similarity	NPC256104
0.7553	Intermediate Similarity	NPC211845
0.7553	Intermediate Similarity	NPC122083
0.7524	Intermediate Similarity	NPC79193
0.75	Intermediate Similarity	NPC125164
0.75	Intermediate Similarity	NPC470156
0.75	Intermediate Similarity	NPC476379
0.75	Intermediate Similarity	NPC211049
0.7475	Intermediate Similarity	NPC80640
0.7473	Intermediate Similarity	NPC471411
0.7473	Intermediate Similarity	NPC471410
0.7473	Intermediate Similarity	NPC228593
0.7473	Intermediate Similarity	NPC474008
0.7473	Intermediate Similarity	NPC235196
0.7451	Intermediate Similarity	NPC207693
0.7449	Intermediate Similarity	NPC477655
0.7449	Intermediate Similarity	NPC80417
0.7449	Intermediate Similarity	NPC477656
0.7423	Intermediate Similarity	NPC472273
0.7423	Intermediate Similarity	NPC266417
0.7419	Intermediate Similarity	NPC200580
0.7419	Intermediate Similarity	NPC471459
0.7419	Intermediate Similarity	NPC67653
0.7419	Intermediate Similarity	NPC477440
0.7419	Intermediate Similarity	NPC477443
0.7416	Intermediate Similarity	NPC470155
0.7416	Intermediate Similarity	NPC477447
0.7416	Intermediate Similarity	NPC212340
0.7416	Intermediate Similarity	NPC477446
0.74	Intermediate Similarity	NPC107385
0.74	Intermediate Similarity	NPC72842
0.7391	Intermediate Similarity	NPC239938
0.7386	Intermediate Similarity	NPC471217
0.7386	Intermediate Similarity	NPC472943
0.7386	Intermediate Similarity	NPC471216
0.7386	Intermediate Similarity	NPC472951
0.7386	Intermediate Similarity	NPC134227
0.7381	Intermediate Similarity	NPC474755
0.7379	Intermediate Similarity	NPC22709
0.7374	Intermediate Similarity	NPC298266
0.7374	Intermediate Similarity	NPC98225
0.7374	Intermediate Similarity	NPC259654
0.7374	Intermediate Similarity	NPC178853
0.7363	Intermediate Similarity	NPC477445
0.7363	Intermediate Similarity	NPC235402
0.734	Intermediate Similarity	NPC477444
0.734	Intermediate Similarity	NPC185529
0.734	Intermediate Similarity	NPC472146
0.734	Intermediate Similarity	NPC477433
0.734	Intermediate Similarity	NPC477442
0.7333	Intermediate Similarity	NPC227170
0.7327	Intermediate Similarity	NPC470167
0.7327	Intermediate Similarity	NPC473526
0.7327	Intermediate Similarity	NPC469827
0.7327	Intermediate Similarity	NPC267637
0.7327	Intermediate Similarity	NPC473701
0.7326	Intermediate Similarity	NPC136424
0.732	Intermediate Similarity	NPC256227
0.732	Intermediate Similarity	NPC235109
0.7317	Intermediate Similarity	NPC119838
0.7308	Intermediate Similarity	NPC470622
0.7308	Intermediate Similarity	NPC475463
0.7303	Intermediate Similarity	NPC116320
0.7303	Intermediate Similarity	NPC119922
0.7303	Intermediate Similarity	NPC470154
0.7303	Intermediate Similarity	NPC71541
0.7294	Intermediate Similarity	NPC55508
0.7294	Intermediate Similarity	NPC477867
0.7292	Intermediate Similarity	NPC309127
0.7292	Intermediate Similarity	NPC247877
0.7292	Intermediate Similarity	NPC470424
0.729	Intermediate Similarity	NPC475490
0.7283	Intermediate Similarity	NPC268633
0.7282	Intermediate Similarity	NPC473410
0.7282	Intermediate Similarity	NPC63841
0.7282	Intermediate Similarity	NPC469984
0.7282	Intermediate Similarity	NPC471094
0.7263	Intermediate Similarity	NPC216137
0.7255	Intermediate Similarity	NPC273189
0.7255	Intermediate Similarity	NPC184805
0.7255	Intermediate Similarity	NPC56656
0.7253	Intermediate Similarity	NPC471044
0.7253	Intermediate Similarity	NPC473336
0.7245	Intermediate Similarity	NPC328180
0.7245	Intermediate Similarity	NPC278028
0.7241	Intermediate Similarity	NPC143250
0.7238	Intermediate Similarity	NPC272242
0.7228	Intermediate Similarity	NPC99510
0.7222	Intermediate Similarity	NPC242771
0.7222	Intermediate Similarity	NPC121121
0.7222	Intermediate Similarity	NPC164289
0.7222	Intermediate Similarity	NPC100366
0.7222	Intermediate Similarity	NPC311642
0.7216	Intermediate Similarity	NPC17336
0.7216	Intermediate Similarity	NPC82633
0.7212	Intermediate Similarity	NPC102741
0.7212	Intermediate Similarity	NPC131903
0.7209	Intermediate Similarity	NPC179922
0.7204	Intermediate Similarity	NPC470920
0.72	Intermediate Similarity	NPC84042
0.72	Intermediate Similarity	NPC308824
0.72	Intermediate Similarity	NPC305085
0.7195	Intermediate Similarity	NPC469925
0.7191	Intermediate Similarity	NPC60568
0.7191	Intermediate Similarity	NPC186588
0.7188	Intermediate Similarity	NPC472232
0.7188	Intermediate Similarity	NPC476189
0.7188	Intermediate Similarity	NPC472231
0.7184	Intermediate Similarity	NPC471474
0.7184	Intermediate Similarity	NPC186054
0.7184	Intermediate Similarity	NPC293512
0.7184	Intermediate Similarity	NPC471430
0.7174	Intermediate Similarity	NPC131350
0.7174	Intermediate Similarity	NPC477205
0.7172	Intermediate Similarity	NPC274695
0.717	Intermediate Similarity	NPC157571
0.7159	Intermediate Similarity	NPC470014
0.7159	Intermediate Similarity	NPC43463
0.7158	Intermediate Similarity	NPC153853
0.7157	Intermediate Similarity	NPC88469
0.7157	Intermediate Similarity	NPC283850
0.7143	Intermediate Similarity	NPC98633
0.7143	Intermediate Similarity	NPC137104
0.7143	Intermediate Similarity	NPC85391
0.7143	Intermediate Similarity	NPC474284
0.7143	Intermediate Similarity	NPC471093
0.7143	Intermediate Similarity	NPC320383
0.7143	Intermediate Similarity	NPC98069
0.7143	Intermediate Similarity	NPC157328
0.7143	Intermediate Similarity	NPC163685
0.7143	Intermediate Similarity	NPC476721
0.7143	Intermediate Similarity	NPC474253
0.7143	Intermediate Similarity	NPC49730
0.7143	Intermediate Similarity	NPC474346
0.7143	Intermediate Similarity	NPC476728
0.7143	Intermediate Similarity	NPC475820
0.7143	Intermediate Similarity	NPC474786
0.7143	Intermediate Similarity	NPC213737
0.7128	Intermediate Similarity	NPC56777
0.7128	Intermediate Similarity	NPC128475
0.7128	Intermediate Similarity	NPC201607
0.7126	Intermediate Similarity	NPC474020
0.7115	Intermediate Similarity	NPC469826
0.7103	Intermediate Similarity	NPC97002

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 NPC478111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	501
0.1-0.2	3511
0.2-0.3	3306
0.3-0.4	1063
0.4-0.5	471
0.5-0.6	255
0.6-0.7	41
0.7-0.8	2
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
0.7551	Intermediate Similarity	NPD1700	Approved
0.7317	Intermediate Similarity	NPD229	Approved
0.7143	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6118	Approved
0.6778	Remote Similarity	NPD6114	Approved
0.6778	Remote Similarity	NPD6115	Approved
0.6778	Remote Similarity	NPD6697	Approved
0.6739	Remote Similarity	NPD1780	Approved
0.6739	Remote Similarity	NPD1779	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6607	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3669	Approved
0.6593	Remote Similarity	NPD4802	Phase 2
0.6593	Remote Similarity	NPD4238	Approved
0.6556	Remote Similarity	NPD6117	Approved
0.6429	Remote Similarity	NPD371	Approved
0.6422	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7492	Approved
0.6346	Remote Similarity	NPD4225	Approved
0.6339	Remote Similarity	NPD8133	Approved
0.6337	Remote Similarity	NPD8171	Discontinued
0.6333	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6686	Approved
0.6303	Remote Similarity	NPD6616	Approved
0.6293	Remote Similarity	NPD6054	Approved
0.6293	Remote Similarity	NPD6059	Approved
0.6277	Remote Similarity	NPD6928	Phase 2
0.6271	Remote Similarity	NPD8328	Phase 3
0.6264	Remote Similarity	NPD3703	Phase 2
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD6016	Approved
0.6239	Remote Similarity	NPD6015	Approved
0.6228	Remote Similarity	NPD6940	Discontinued
0.6216	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD897	Approved
0.6207	Remote Similarity	NPD898	Approved
0.6207	Remote Similarity	NPD896	Approved
0.6198	Remote Similarity	NPD7736	Approved
0.6186	Remote Similarity	NPD6370	Approved
0.6186	Remote Similarity	NPD5988	Approved
0.6168	Remote Similarity	NPD8086	Approved
0.6168	Remote Similarity	NPD8139	Approved
0.6168	Remote Similarity	NPD8085	Approved
0.6168	Remote Similarity	NPD8138	Approved
0.6168	Remote Similarity	NPD8084	Approved
0.6168	Remote Similarity	NPD8083	Approved
0.6168	Remote Similarity	NPD8082	Approved
0.6154	Remote Similarity	NPD1811	Approved
0.6154	Remote Similarity	NPD1810	Approved
0.6148	Remote Similarity	NPD7319	Approved
0.6111	Remote Similarity	NPD8276	Approved
0.6111	Remote Similarity	NPD8275	Approved
0.6102	Remote Similarity	NPD6921	Approved
0.6091	Remote Similarity	NPD6412	Phase 2
0.6078	Remote Similarity	NPD8034	Phase 2
0.6078	Remote Similarity	NPD8035	Phase 2
0.6067	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8081	Approved
0.6047	Remote Similarity	NPD7909	Approved
0.6033	Remote Similarity	NPD7507	Approved
0.6017	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD8393	Approved
0.5976	Remote Similarity	NPD2267	Suspended
0.5966	Remote Similarity	NPD8517	Approved
0.5966	Remote Similarity	NPD8515	Approved
0.5966	Remote Similarity	NPD8513	Phase 3
0.5966	Remote Similarity	NPD8516	Approved
0.5962	Remote Similarity	NPD5282	Discontinued
0.5946	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3728	Approved
0.5926	Remote Similarity	NPD3730	Approved
0.5914	Remote Similarity	NPD3702	Approved
0.5905	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6009	Approved
0.5806	Remote Similarity	NPD6033	Approved
0.5804	Remote Similarity	NPD8307	Discontinued
0.5804	Remote Similarity	NPD8140	Approved
0.5804	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7516	Approved
0.5795	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6371	Approved
0.5784	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD4632	Approved
0.5769	Remote Similarity	NPD7983	Approved
0.5769	Remote Similarity	NPD6411	Approved
0.5765	Remote Similarity	NPD3198	Approved
0.5763	Remote Similarity	NPD7115	Discovery
0.5761	Remote Similarity	NPD5777	Approved
0.5747	Remote Similarity	NPD8961	Approved
0.5745	Remote Similarity	NPD2257	Approved
0.5741	Remote Similarity	NPD7638	Approved
0.5739	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6067	Discontinued
0.5732	Remote Similarity	NPD615	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4224	Phase 2
0.5726	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD3698	Phase 2
0.5714	Remote Similarity	NPD7328	Approved
0.5714	Remote Similarity	NPD5779	Approved
0.5714	Remote Similarity	NPD5778	Approved
0.5714	Remote Similarity	NPD8959	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD8306	Approved
0.5702	Remote Similarity	NPD8305	Approved
0.569	Remote Similarity	NPD6882	Approved
0.5688	Remote Similarity	NPD7639	Approved
0.5688	Remote Similarity	NPD7640	Approved
0.5673	Remote Similarity	NPD46	Approved
0.5673	Remote Similarity	NPD6698	Approved
0.567	Remote Similarity	NPD7329	Approved
0.5652	Remote Similarity	NPD4245	Approved
0.5652	Remote Similarity	NPD4244	Approved
0.5652	Remote Similarity	NPD2686	Approved
0.5652	Remote Similarity	NPD2687	Approved
0.5652	Remote Similarity	NPD8087	Discontinued
0.5652	Remote Similarity	NPD2254	Approved
0.5648	Remote Similarity	NPD7902	Approved
0.5636	Remote Similarity	NPD5344	Discontinued
0.562	Remote Similarity	NPD8294	Approved
0.562	Remote Similarity	NPD8377	Approved
0.5614	Remote Similarity	NPD7320	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