NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	254.634
LogP:	3.458
LogD:	2.603
LogS:	-3.16
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	4.837
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.848
MDCK Permeability:	2.9920762244728394e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.678
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	89.81655883789062%
Volume Distribution (VD):	2.469
Pgp-substrate:	15.324434280395508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.561
CYP2C19-inhibitor:	0.683
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.452
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.917
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	5.085
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.672
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.702
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.342
Carcinogencity:	0.956
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC102463

Natural Product ID:	NPC102463
*Common Name:**	FMUFYIFXWSUYSC-XXLQHYSLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FMUFYIFXWSUYSC-XXLQHYSLSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9-5-6-11-12-10(9)7-17-8-15(12,4)13(16)14(11,2)3/h7,9,13,16H,5-6,8H2,1-4H3/t9-,13-,15-/m1/s1
SMILES:	C[C@@H]1CCC2=C3C1=COC[C@@]3(C)[C@@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482040
PubChem CID:	11345345
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	isolated from the marine red alga Polysiphonia	n.a.	PMID[15787444]
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917307]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	0.0	mm	PMID[546085]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	6.0	mm	PMID[546085]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	0.0	mm	PMID[546085]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	0.0	mm	PMID[546085]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	5.0	mm	PMID[546085]

☑ 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 NPC102463 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	166
0.1-0.2	1338
0.2-0.3	6503
0.3-0.4	17856
0.4-0.5	10440
0.5-0.6	5375
0.6-0.7	965
0.7-0.8	52
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC31258
0.7778	Intermediate Similarity	NPC5985
0.7692	Intermediate Similarity	NPC96319
0.7561	Intermediate Similarity	NPC201852
0.7532	Intermediate Similarity	NPC474140
0.75	Intermediate Similarity	NPC477522
0.75	Intermediate Similarity	NPC76931
0.75	Intermediate Similarity	NPC318136
0.75	Intermediate Similarity	NPC18603
0.75	Intermediate Similarity	NPC92801
0.75	Intermediate Similarity	NPC307965
0.747	Intermediate Similarity	NPC470384
0.7468	Intermediate Similarity	NPC321016
0.7468	Intermediate Similarity	NPC107059
0.7468	Intermediate Similarity	NPC321381
0.7467	Intermediate Similarity	NPC208999
0.7436	Intermediate Similarity	NPC471797
0.7436	Intermediate Similarity	NPC27395
0.7436	Intermediate Similarity	NPC329090
0.7429	Intermediate Similarity	NPC475830
0.7375	Intermediate Similarity	NPC155986
0.7375	Intermediate Similarity	NPC198968
0.7375	Intermediate Similarity	NPC318495
0.7368	Intermediate Similarity	NPC471560
0.7368	Intermediate Similarity	NPC90115
0.7368	Intermediate Similarity	NPC217570
0.7342	Intermediate Similarity	NPC22105
0.7342	Intermediate Similarity	NPC471468
0.7342	Intermediate Similarity	NPC136188
0.7342	Intermediate Similarity	NPC285893
0.7342	Intermediate Similarity	NPC230301
0.7342	Intermediate Similarity	NPC304309
0.7342	Intermediate Similarity	NPC319090
0.7342	Intermediate Similarity	NPC28657
0.7342	Intermediate Similarity	NPC288035
0.7342	Intermediate Similarity	NPC134847
0.7342	Intermediate Similarity	NPC328104
0.7342	Intermediate Similarity	NPC162742
0.7333	Intermediate Similarity	NPC477791
0.7317	Intermediate Similarity	NPC26117
0.7308	Intermediate Similarity	NPC130665
0.7308	Intermediate Similarity	NPC471799
0.7294	Intermediate Similarity	NPC474189
0.7294	Intermediate Similarity	NPC474349
0.7284	Intermediate Similarity	NPC473943
0.7284	Intermediate Similarity	NPC87604
0.7284	Intermediate Similarity	NPC477514
0.7284	Intermediate Similarity	NPC186191
0.7284	Intermediate Similarity	NPC205455
0.7284	Intermediate Similarity	NPC275910
0.7284	Intermediate Similarity	NPC474216
0.7273	Intermediate Similarity	NPC34834
0.726	Intermediate Similarity	NPC133368
0.726	Intermediate Similarity	NPC211291
0.725	Intermediate Similarity	NPC113733
0.725	Intermediate Similarity	NPC300324
0.725	Intermediate Similarity	NPC73875
0.725	Intermediate Similarity	NPC240604
0.725	Intermediate Similarity	NPC315261
0.7241	Intermediate Similarity	NPC2158
0.7237	Intermediate Similarity	NPC216460
0.7229	Intermediate Similarity	NPC82986
0.7229	Intermediate Similarity	NPC7505
0.7229	Intermediate Similarity	NPC470383
0.7229	Intermediate Similarity	NPC474752
0.7229	Intermediate Similarity	NPC474683
0.7229	Intermediate Similarity	NPC474759
0.7229	Intermediate Similarity	NPC474731
0.72	Intermediate Similarity	NPC272125
0.72	Intermediate Similarity	NPC202017
0.7195	Intermediate Similarity	NPC47982
0.7195	Intermediate Similarity	NPC109546
0.7195	Intermediate Similarity	NPC472463
0.7195	Intermediate Similarity	NPC84694
0.7195	Intermediate Similarity	NPC143182
0.7195	Intermediate Similarity	NPC28862
0.7195	Intermediate Similarity	NPC1319
0.7195	Intermediate Similarity	NPC155924
0.7195	Intermediate Similarity	NPC81306
0.7195	Intermediate Similarity	NPC328714
0.7179	Intermediate Similarity	NPC242001
0.7179	Intermediate Similarity	NPC164022
0.7176	Intermediate Similarity	NPC238485
0.7176	Intermediate Similarity	NPC474493
0.7162	Intermediate Similarity	NPC290367
0.7162	Intermediate Similarity	NPC323424
0.7162	Intermediate Similarity	NPC96793
0.7162	Intermediate Similarity	NPC110241
0.716	Intermediate Similarity	NPC214570
0.716	Intermediate Similarity	NPC34019
0.7143	Intermediate Similarity	NPC101462
0.7143	Intermediate Similarity	NPC20853
0.7143	Intermediate Similarity	NPC202389
0.7143	Intermediate Similarity	NPC248886
0.7143	Intermediate Similarity	NPC470614
0.7143	Intermediate Similarity	NPC167272
0.7143	Intermediate Similarity	NPC269877
0.7143	Intermediate Similarity	NPC1272
0.7143	Intermediate Similarity	NPC474248
0.7126	Intermediate Similarity	NPC271967
0.7125	Intermediate Similarity	NPC257347
0.7125	Intermediate Similarity	NPC118508
0.7125	Intermediate Similarity	NPC141071
0.7125	Intermediate Similarity	NPC322353
0.7125	Intermediate Similarity	NPC121744
0.7125	Intermediate Similarity	NPC60818
0.7125	Intermediate Similarity	NPC471723
0.7125	Intermediate Similarity	NPC23231
0.7108	Intermediate Similarity	NPC241290
0.7108	Intermediate Similarity	NPC324772
0.7108	Intermediate Similarity	NPC209944
0.7108	Intermediate Similarity	NPC234193
0.7108	Intermediate Similarity	NPC164840
0.7105	Intermediate Similarity	NPC472253
0.7105	Intermediate Similarity	NPC472255
0.7105	Intermediate Similarity	NPC114651
0.7093	Intermediate Similarity	NPC266511
0.7089	Intermediate Similarity	NPC220939
0.7089	Intermediate Similarity	NPC68443
0.7089	Intermediate Similarity	NPC265485
0.7067	Intermediate Similarity	NPC208198
0.7067	Intermediate Similarity	NPC2728
0.7067	Intermediate Similarity	NPC60837
0.7067	Intermediate Similarity	NPC172613
0.7067	Intermediate Similarity	NPC11555
0.7067	Intermediate Similarity	NPC238352
0.7067	Intermediate Similarity	NPC282619
0.7067	Intermediate Similarity	NPC477009
0.7059	Intermediate Similarity	NPC237795
0.7059	Intermediate Similarity	NPC475789
0.7059	Intermediate Similarity	NPC82538
0.7051	Intermediate Similarity	NPC49422
0.7051	Intermediate Similarity	NPC9161
0.7051	Intermediate Similarity	NPC145498
0.7045	Intermediate Similarity	NPC470542
0.7037	Intermediate Similarity	NPC134330
0.7037	Intermediate Similarity	NPC265588
0.7037	Intermediate Similarity	NPC244488
0.7037	Intermediate Similarity	NPC470362
0.7037	Intermediate Similarity	NPC189883
0.7037	Intermediate Similarity	NPC129165
0.7037	Intermediate Similarity	NPC202642
0.7037	Intermediate Similarity	NPC247325
0.7037	Intermediate Similarity	NPC106432
0.7037	Intermediate Similarity	NPC46160
0.7024	Intermediate Similarity	NPC23852
0.7024	Intermediate Similarity	NPC264245
0.7024	Intermediate Similarity	NPC209620
0.7024	Intermediate Similarity	NPC6707
0.7024	Intermediate Similarity	NPC474531
0.7024	Intermediate Similarity	NPC6434
0.7024	Intermediate Similarity	NPC47761
0.7024	Intermediate Similarity	NPC320525
0.7013	Intermediate Similarity	NPC96484
0.7013	Intermediate Similarity	NPC160209
0.7013	Intermediate Similarity	NPC276616
0.7013	Intermediate Similarity	NPC32055
0.7013	Intermediate Similarity	NPC167527
0.7011	Intermediate Similarity	NPC152808
0.7011	Intermediate Similarity	NPC293287
0.7	Intermediate Similarity	NPC469534
0.7	Intermediate Similarity	NPC469533
0.7	Intermediate Similarity	NPC91858
0.7	Intermediate Similarity	NPC477138
0.7	Intermediate Similarity	NPC243342
0.7	Intermediate Similarity	NPC469593
0.6988	Remote Similarity	NPC53744
0.6988	Remote Similarity	NPC30986
0.6988	Remote Similarity	NPC209430
0.6977	Remote Similarity	NPC205845
0.6977	Remote Similarity	NPC185568
0.6977	Remote Similarity	NPC209802
0.6977	Remote Similarity	NPC124172
0.6977	Remote Similarity	NPC231310
0.6974	Remote Similarity	NPC149680
0.6962	Remote Similarity	NPC167706
0.6962	Remote Similarity	NPC242992
0.6962	Remote Similarity	NPC469343
0.6951	Remote Similarity	NPC91594
0.6951	Remote Similarity	NPC471798
0.6951	Remote Similarity	NPC283619
0.6951	Remote Similarity	NPC477924
0.6941	Remote Similarity	NPC49964
0.6941	Remote Similarity	NPC470049
0.6941	Remote Similarity	NPC151519
0.6941	Remote Similarity	NPC189972
0.6941	Remote Similarity	NPC50964
0.6941	Remote Similarity	NPC30166
0.6933	Remote Similarity	NPC101128
0.6933	Remote Similarity	NPC144650
0.6932	Remote Similarity	NPC149224
0.6923	Remote Similarity	NPC472942
0.6923	Remote Similarity	NPC473893
0.6914	Remote Similarity	NPC66566
0.6914	Remote Similarity	NPC133580
0.6914	Remote Similarity	NPC171148
0.6914	Remote Similarity	NPC291503
0.6914	Remote Similarity	NPC69383
0.6914	Remote Similarity	NPC313185
0.6914	Remote Similarity	NPC477923

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 NPC102463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1880
0.2-0.3	4115
0.3-0.4	2201
0.4-0.5	605
0.5-0.6	147
0.6-0.7	51
0.7-0.8	4
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
0.7692	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6924	Approved
0.7436	Intermediate Similarity	NPD6926	Approved
0.7342	Intermediate Similarity	NPD6942	Approved
0.7342	Intermediate Similarity	NPD7339	Approved
0.725	Intermediate Similarity	NPD6933	Approved
0.7195	Intermediate Similarity	NPD6929	Approved
0.7143	Intermediate Similarity	NPD6923	Approved
0.7143	Intermediate Similarity	NPD6922	Approved
0.7108	Intermediate Similarity	NPD6931	Approved
0.7108	Intermediate Similarity	NPD6930	Phase 2
0.7108	Intermediate Similarity	NPD7509	Discontinued
0.7059	Intermediate Similarity	NPD6695	Phase 3
0.7051	Intermediate Similarity	NPD7144	Approved
0.7051	Intermediate Similarity	NPD7143	Approved
0.6988	Remote Similarity	NPD7645	Phase 2
0.6977	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7152	Approved
0.6962	Remote Similarity	NPD7150	Approved
0.6962	Remote Similarity	NPD7151	Approved
0.6951	Remote Similarity	NPD6925	Approved
0.6951	Remote Similarity	NPD6932	Approved
0.6951	Remote Similarity	NPD5776	Phase 2
0.6941	Remote Similarity	NPD3667	Approved
0.6914	Remote Similarity	NPD8264	Approved
0.6905	Remote Similarity	NPD7332	Phase 2
0.6905	Remote Similarity	NPD4748	Discontinued
0.6867	Remote Similarity	NPD7145	Approved
0.6867	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6898	Phase 1
0.679	Remote Similarity	NPD4784	Approved
0.679	Remote Similarity	NPD4785	Approved
0.6786	Remote Similarity	NPD6683	Phase 2
0.6782	Remote Similarity	NPD3666	Approved
0.6782	Remote Similarity	NPD4786	Approved
0.6782	Remote Similarity	NPD3133	Approved
0.6782	Remote Similarity	NPD3665	Phase 1
0.675	Remote Similarity	NPD4243	Approved
0.6742	Remote Similarity	NPD7750	Discontinued
0.6742	Remote Similarity	NPD7524	Approved
0.6742	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7514	Phase 3
0.6706	Remote Similarity	NPD7525	Registered
0.6705	Remote Similarity	NPD6893	Approved
0.6629	Remote Similarity	NPD5279	Phase 3
0.6628	Remote Similarity	NPD6902	Approved
0.6528	Remote Similarity	NPD342	Phase 1
0.6506	Remote Similarity	NPD4190	Phase 3
0.6506	Remote Similarity	NPD5275	Approved
0.6477	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD7087	Discontinued
0.6447	Remote Similarity	NPD368	Approved
0.6444	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD1346	Approved
0.6413	Remote Similarity	NPD4753	Phase 2
0.6395	Remote Similarity	NPD4195	Approved
0.6277	Remote Similarity	NPD6411	Approved
0.6264	Remote Similarity	NPD5280	Approved
0.6264	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD3668	Phase 3
0.6211	Remote Similarity	NPD4202	Approved
0.6211	Remote Similarity	NPD6399	Phase 3
0.618	Remote Similarity	NPD4223	Phase 3
0.618	Remote Similarity	NPD4221	Approved
0.617	Remote Similarity	NPD7136	Phase 2
0.6154	Remote Similarity	NPD1696	Phase 3
0.6122	Remote Similarity	NPD6084	Phase 2
0.6122	Remote Similarity	NPD4755	Approved
0.6122	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD4788	Approved
0.6105	Remote Similarity	NPD6079	Approved
0.6105	Remote Similarity	NPD7637	Suspended
0.61	Remote Similarity	NPD4159	Approved
0.6098	Remote Similarity	NPD15	Approved
0.6098	Remote Similarity	NPD791	Approved
0.6092	Remote Similarity	NPD3617	Approved
0.6087	Remote Similarity	NPD7521	Approved
0.6087	Remote Similarity	NPD7334	Approved
0.6087	Remote Similarity	NPD6409	Approved
0.6087	Remote Similarity	NPD5330	Approved
0.6087	Remote Similarity	NPD7146	Approved
0.6087	Remote Similarity	NPD6684	Approved
0.6082	Remote Similarity	NPD5210	Approved
0.6082	Remote Similarity	NPD5695	Phase 3
0.6082	Remote Similarity	NPD4629	Approved
0.6071	Remote Similarity	NPD4732	Discontinued
0.6064	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6101	Approved
0.6044	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD4219	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD5285	Approved
0.5979	Remote Similarity	NPD5282	Discontinued
0.5978	Remote Similarity	NPD5329	Approved
0.5957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6903	Approved
0.5957	Remote Similarity	NPD4518	Approved
0.5955	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4695	Discontinued
0.5938	Remote Similarity	NPD5281	Approved
0.5938	Remote Similarity	NPD5284	Approved
0.5934	Remote Similarity	NPD5362	Discontinued
0.5914	Remote Similarity	NPD4693	Phase 3
0.5914	Remote Similarity	NPD4688	Approved
0.5914	Remote Similarity	NPD4689	Approved
0.5914	Remote Similarity	NPD4138	Approved
0.5914	Remote Similarity	NPD5690	Phase 2
0.5914	Remote Similarity	NPD5205	Approved
0.5914	Remote Similarity	NPD4690	Approved
0.59	Remote Similarity	NPD7638	Approved
0.59	Remote Similarity	NPD5696	Approved
0.5895	Remote Similarity	NPD6051	Approved
0.5889	Remote Similarity	NPD4692	Approved
0.5889	Remote Similarity	NPD4139	Approved
0.5882	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD5225	Approved
0.5882	Remote Similarity	NPD5226	Approved
0.5882	Remote Similarity	NPD5224	Approved
0.5882	Remote Similarity	NPD4633	Approved
0.5876	Remote Similarity	NPD5779	Approved
0.5876	Remote Similarity	NPD5778	Approved
0.5865	Remote Similarity	NPD7128	Approved
0.5865	Remote Similarity	NPD6402	Approved
0.5865	Remote Similarity	NPD6675	Approved
0.5865	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD5221	Approved
0.5859	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4697	Phase 3
0.5859	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD7639	Approved
0.5842	Remote Similarity	NPD7640	Approved
0.5841	Remote Similarity	NPD7503	Approved
0.5833	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4096	Approved
0.5833	Remote Similarity	NPD6053	Discontinued
0.5825	Remote Similarity	NPD5174	Approved
0.5825	Remote Similarity	NPD5175	Approved
0.581	Remote Similarity	NPD6412	Phase 2
0.581	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD5697	Approved
0.5806	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5173	Approved
0.5789	Remote Similarity	NPD4723	Approved
0.5789	Remote Similarity	NPD4722	Approved
0.5784	Remote Similarity	NPD5223	Approved
0.5778	Remote Similarity	NPD4822	Approved
0.5778	Remote Similarity	NPD4821	Approved
0.5778	Remote Similarity	NPD4820	Approved
0.5778	Remote Similarity	NPD4819	Approved
0.5778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7515	Phase 2
0.5769	Remote Similarity	NPD5141	Approved
0.5755	Remote Similarity	NPD7320	Approved
0.5755	Remote Similarity	NPD6899	Approved
0.5755	Remote Similarity	NPD6881	Approved
0.5745	Remote Similarity	NPD4249	Approved
0.5745	Remote Similarity	NPD4519	Discontinued
0.5745	Remote Similarity	NPD4623	Approved
0.5743	Remote Similarity	NPD4225	Approved
0.5743	Remote Similarity	NPD5290	Discontinued
0.573	Remote Similarity	NPD4268	Approved
0.573	Remote Similarity	NPD4271	Approved
0.5729	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4768	Approved
0.5714	Remote Similarity	NPD1082	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD5133	Approved
0.5714	Remote Similarity	NPD6640	Phase 3
0.5714	Remote Similarity	NPD5369	Approved
0.5701	Remote Similarity	NPD6372	Approved
0.5701	Remote Similarity	NPD6013	Approved
0.5701	Remote Similarity	NPD6014	Approved
0.5701	Remote Similarity	NPD6012	Approved
0.5701	Remote Similarity	NPD6373	Approved
0.5696	Remote Similarity	NPD1145	Discontinued
0.5684	Remote Similarity	NPD4250	Approved
0.5684	Remote Similarity	NPD4251	Approved
0.5673	Remote Similarity	NPD4754	Approved
0.567	Remote Similarity	NPD5692	Phase 3
0.567	Remote Similarity	NPD5207	Approved
0.5657	Remote Similarity	NPD7748	Approved
0.5652	Remote Similarity	NPD6435	Approved
0.5648	Remote Similarity	NPD6883	Approved
0.5648	Remote Similarity	NPD7290	Approved
0.5648	Remote Similarity	NPD7102	Approved
0.5625	Remote Similarity	NPD6672	Approved
0.5625	Remote Similarity	NPD5737	Approved
0.5612	Remote Similarity	NPD6050	Approved
0.5612	Remote Similarity	NPD5694	Approved
0.5607	Remote Similarity	NPD5128	Approved
0.5607	Remote Similarity	NPD4730	Approved
0.5607	Remote Similarity	NPD6011	Approved
0.5607	Remote Similarity	NPD4729	Approved
0.5604	Remote Similarity	NPD5368	Approved
0.56	Remote Similarity	NPD1698	Clinical (unspecified phase)

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