NPASS Compound

Structure

NPC310643 OpenBabel07101719142D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.4680 3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4677 0.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7985 -0.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7953 0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 -0.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4895 0.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 1.2308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 10 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 13 2 1 1 0 0 0 13 17 1 0 0 0 0 14 12 1 6 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 1 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.252
LogD:	3.68
LogS:	-3.675
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	5.049
Fsp3:	0.8
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:	-4.368
MDCK Permeability:	6.195550668053329e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.613
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.524
Plasma Protein Binding (PPB):	80.74388122558594%
Volume Distribution (VD):	0.838
Pgp-substrate:	15.575679779052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.531
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.513
CYP3A4-inhibitor:	0.318
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	7.993
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.418
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.069
Carcinogencity:	0.008
Eye Corrosion:	0.061
Eye Irritation:	0.593
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC310643

Natural Product ID:	NPC310643
*Common Name:**	UNFATVMRCUCOCE-ZNIAXHAMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UNFATVMRCUCOCE-ZNIAXHAMSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-12(7-6-10-19(3,4)22)14-11-16(21)20(5)15-9-8-13(2)17(15)18(14)20/h6,10,13-18,21-22H,1,7-9,11H2,2-5H3/b10-6+/t13-,14+,15+,16-,17-,18+,20+/m1/s1
SMILES:	C=C(C/C=C/C(C)(C)O)[C@@H]1C[C@H]([C@]2(C)[C@H]3CC[C@@H](C)[C@H]3[C@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3425796
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001595] Spatane and 4,10-secospatane diterpenoids

*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
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	Eukaryota	n.a.	At a depth of 510 m, Gulf of Mannar near Mandapam coast (9 16'N, 79 12'E), Tamilnadu, India	2013-May	PMID[25978960]
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	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
MIC	4
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	50.04	ug.mL-1	PMID[452898]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	100.0	ug.mL-1	PMID[452898]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	16.0	mm	PMID[452898]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	16.33	mm	PMID[452898]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.67	mm	PMID[452898]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.67	mm	PMID[452898]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	174.11	ug.mL-1	PMID[452898]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	42.31	ug.mL-1	PMID[452898]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	100.0	ug.mL-1	PMID[452898]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	100.0	ug.mL-1	PMID[452898]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[452898]

☑ 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 NPC310643 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	184
0.1-0.2	1821
0.2-0.3	12238
0.3-0.4	13891
0.4-0.5	8260
0.5-0.6	5115
0.6-0.7	1068
0.7-0.8	93
0.8-0.85	18
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC472465
0.8831	High Similarity	NPC472471
0.8767	High Similarity	NPC234527
0.8767	High Similarity	NPC14352
0.8732	High Similarity	NPC224532
0.8649	High Similarity	NPC309178
0.8649	High Similarity	NPC471659
0.8592	High Similarity	NPC477791
0.8571	High Similarity	NPC477009
0.8571	High Similarity	NPC238352
0.8533	High Similarity	NPC313185
0.8429	Intermediate Similarity	NPC309300
0.8421	Intermediate Similarity	NPC471658
0.8378	Intermediate Similarity	NPC471660
0.8378	Intermediate Similarity	NPC471662
0.8375	Intermediate Similarity	NPC472473
0.8333	Intermediate Similarity	NPC472466
0.8333	Intermediate Similarity	NPC136813
0.831	Intermediate Similarity	NPC19569
0.8286	Intermediate Similarity	NPC474480
0.8243	Intermediate Similarity	NPC254845
0.8235	Intermediate Similarity	NPC472468
0.8219	Intermediate Similarity	NPC167527
0.8194	Intermediate Similarity	NPC162309
0.8182	Intermediate Similarity	NPC126969
0.8182	Intermediate Similarity	NPC472472
0.8143	Intermediate Similarity	NPC15152
0.8125	Intermediate Similarity	NPC471661
0.8046	Intermediate Similarity	NPC472467
0.8026	Intermediate Similarity	NPC329763
0.8	Intermediate Similarity	NPC133873
0.8	Intermediate Similarity	NPC252809
0.8	Intermediate Similarity	NPC323153
0.7901	Intermediate Similarity	NPC264245
0.7887	Intermediate Similarity	NPC210346
0.7857	Intermediate Similarity	NPC5698
0.7805	Intermediate Similarity	NPC87489
0.7805	Intermediate Similarity	NPC296701
0.7805	Intermediate Similarity	NPC49964
0.7805	Intermediate Similarity	NPC218616
0.7778	Intermediate Similarity	NPC474155
0.7778	Intermediate Similarity	NPC234193
0.7778	Intermediate Similarity	NPC241290
0.7778	Intermediate Similarity	NPC472470
0.7778	Intermediate Similarity	NPC164840
0.7778	Intermediate Similarity	NPC473759
0.7778	Intermediate Similarity	NPC209944
0.775	Intermediate Similarity	NPC477514
0.7746	Intermediate Similarity	NPC162109
0.7738	Intermediate Similarity	NPC318390
0.7722	Intermediate Similarity	NPC247325
0.7722	Intermediate Similarity	NPC244488
0.7692	Intermediate Similarity	NPC329090
0.7692	Intermediate Similarity	NPC27395
0.7683	Intermediate Similarity	NPC47761
0.7671	Intermediate Similarity	NPC300593
0.7662	Intermediate Similarity	NPC41886
0.7654	Intermediate Similarity	NPC30986
0.7654	Intermediate Similarity	NPC143182
0.7654	Intermediate Similarity	NPC81306
0.7654	Intermediate Similarity	NPC47982
0.7654	Intermediate Similarity	NPC109546
0.7654	Intermediate Similarity	NPC209430
0.7654	Intermediate Similarity	NPC28862
0.7654	Intermediate Similarity	NPC84694
0.7647	Intermediate Similarity	NPC152808
0.7647	Intermediate Similarity	NPC293287
0.7632	Intermediate Similarity	NPC217570
0.7632	Intermediate Similarity	NPC90115
0.7632	Intermediate Similarity	NPC471560
0.7625	Intermediate Similarity	NPC476439
0.7619	Intermediate Similarity	NPC231310
0.7619	Intermediate Similarity	NPC205845
0.7619	Intermediate Similarity	NPC238485
0.7606	Intermediate Similarity	NPC122239
0.7606	Intermediate Similarity	NPC475931
0.76	Intermediate Similarity	NPC472255
0.76	Intermediate Similarity	NPC308522
0.76	Intermediate Similarity	NPC74885
0.76	Intermediate Similarity	NPC472253
0.7595	Intermediate Similarity	NPC23231
0.7595	Intermediate Similarity	NPC328104
0.7595	Intermediate Similarity	NPC60818
0.7595	Intermediate Similarity	NPC113639
0.7595	Intermediate Similarity	NPC319090
0.759	Intermediate Similarity	NPC50964
0.7586	Intermediate Similarity	NPC2983
0.7568	Intermediate Similarity	NPC308844
0.7564	Intermediate Similarity	NPC130665
0.7564	Intermediate Similarity	NPC474140
0.7561	Intermediate Similarity	NPC324772
0.7556	Intermediate Similarity	NPC472469
0.7534	Intermediate Similarity	NPC124112
0.7532	Intermediate Similarity	NPC34834
0.7531	Intermediate Similarity	NPC474216
0.7531	Intermediate Similarity	NPC477522
0.7529	Intermediate Similarity	NPC274448
0.75	Intermediate Similarity	NPC471081
0.75	Intermediate Similarity	NPC315261
0.75	Intermediate Similarity	NPC475789
0.75	Intermediate Similarity	NPC470384
0.75	Intermediate Similarity	NPC474634
0.75	Intermediate Similarity	NPC47840
0.75	Intermediate Similarity	NPC234264
0.75	Intermediate Similarity	NPC82623
0.747	Intermediate Similarity	NPC320525
0.747	Intermediate Similarity	NPC23852
0.747	Intermediate Similarity	NPC209620
0.7467	Intermediate Similarity	NPC267027
0.7467	Intermediate Similarity	NPC272125
0.7465	Intermediate Similarity	NPC181872
0.7442	Intermediate Similarity	NPC261266
0.7442	Intermediate Similarity	NPC139724
0.7439	Intermediate Similarity	NPC1319
0.7432	Intermediate Similarity	NPC287744
0.7432	Intermediate Similarity	NPC140233
0.7412	Intermediate Similarity	NPC474047
0.7412	Intermediate Similarity	NPC470077
0.7407	Intermediate Similarity	NPC155986
0.7407	Intermediate Similarity	NPC198968
0.7407	Intermediate Similarity	NPC318495
0.7403	Intermediate Similarity	NPC22301
0.7403	Intermediate Similarity	NPC474248
0.7397	Intermediate Similarity	NPC63111
0.7386	Intermediate Similarity	NPC170775
0.7381	Intermediate Similarity	NPC202389
0.7381	Intermediate Similarity	NPC189972
0.7381	Intermediate Similarity	NPC101462
0.7368	Intermediate Similarity	NPC73603
0.7368	Intermediate Similarity	NPC68703
0.7368	Intermediate Similarity	NPC69649
0.7368	Intermediate Similarity	NPC114651
0.7356	Intermediate Similarity	NPC149224
0.7349	Intermediate Similarity	NPC26117
0.7342	Intermediate Similarity	NPC472506
0.7333	Intermediate Similarity	NPC37816
0.7326	Intermediate Similarity	NPC470360
0.7326	Intermediate Similarity	NPC157257
0.7317	Intermediate Similarity	NPC470944
0.7317	Intermediate Similarity	NPC475980
0.7317	Intermediate Similarity	NPC285761
0.7317	Intermediate Similarity	NPC473943
0.7308	Intermediate Similarity	NPC9161
0.7308	Intermediate Similarity	NPC471781
0.7308	Intermediate Similarity	NPC49422
0.7308	Intermediate Similarity	NPC470041
0.7303	Intermediate Similarity	NPC320026
0.7297	Intermediate Similarity	NPC279200
0.7294	Intermediate Similarity	NPC317458
0.7294	Intermediate Similarity	NPC477818
0.7294	Intermediate Similarity	NPC470558
0.7294	Intermediate Similarity	NPC320548
0.7294	Intermediate Similarity	NPC134481
0.7294	Intermediate Similarity	NPC477667
0.7294	Intermediate Similarity	NPC471340
0.7284	Intermediate Similarity	NPC107059
0.7284	Intermediate Similarity	NPC476317
0.7284	Intermediate Similarity	NPC265588
0.7284	Intermediate Similarity	NPC134330
0.7284	Intermediate Similarity	NPC321381
0.7284	Intermediate Similarity	NPC129165
0.7284	Intermediate Similarity	NPC113733
0.7284	Intermediate Similarity	NPC96319
0.7284	Intermediate Similarity	NPC470362
0.7284	Intermediate Similarity	NPC321016
0.7273	Intermediate Similarity	NPC160209
0.7273	Intermediate Similarity	NPC133588
0.7273	Intermediate Similarity	NPC471238
0.7273	Intermediate Similarity	NPC471952
0.7262	Intermediate Similarity	NPC7505
0.7262	Intermediate Similarity	NPC474731
0.7262	Intermediate Similarity	NPC474752
0.7262	Intermediate Similarity	NPC474683
0.7262	Intermediate Similarity	NPC474759
0.7262	Intermediate Similarity	NPC82986
0.726	Intermediate Similarity	NPC66020
0.725	Intermediate Similarity	NPC469534
0.725	Intermediate Similarity	NPC469533
0.725	Intermediate Similarity	NPC476366
0.725	Intermediate Similarity	NPC469593
0.725	Intermediate Similarity	NPC201048
0.725	Intermediate Similarity	NPC306727
0.7241	Intermediate Similarity	NPC477668
0.7241	Intermediate Similarity	NPC469994
0.7241	Intermediate Similarity	NPC6391
0.7241	Intermediate Similarity	NPC299068
0.7237	Intermediate Similarity	NPC476406
0.7237	Intermediate Similarity	NPC135650
0.7229	Intermediate Similarity	NPC328714
0.7229	Intermediate Similarity	NPC80530
0.7229	Intermediate Similarity	NPC273410
0.7222	Intermediate Similarity	NPC226848
0.7215	Intermediate Similarity	NPC164045
0.7215	Intermediate Similarity	NPC471272
0.7209	Intermediate Similarity	NPC185568
0.72	Intermediate Similarity	NPC219940
0.72	Intermediate Similarity	NPC110241
0.72	Intermediate Similarity	NPC475704
0.72	Intermediate Similarity	NPC225415
0.72	Intermediate Similarity	NPC107540

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 NPC310643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	2356
0.2-0.3	4475
0.3-0.4	1562
0.4-0.5	296
0.5-0.6	217
0.6-0.7	71
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
0.7711	Intermediate Similarity	NPD5331	Approved
0.7711	Intermediate Similarity	NPD5332	Approved
0.7692	Intermediate Similarity	NPD6924	Approved
0.7692	Intermediate Similarity	NPD6926	Approved
0.7683	Intermediate Similarity	NPD4790	Discontinued
0.7561	Intermediate Similarity	NPD7514	Phase 3
0.7561	Intermediate Similarity	NPD6930	Phase 2
0.7561	Intermediate Similarity	NPD6931	Approved
0.7531	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5362	Discontinued
0.75	Intermediate Similarity	NPD6933	Approved
0.7439	Intermediate Similarity	NPD6929	Approved
0.7356	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4820	Approved
0.7349	Intermediate Similarity	NPD4822	Approved
0.7349	Intermediate Similarity	NPD4819	Approved
0.7349	Intermediate Similarity	NPD7332	Phase 2
0.7349	Intermediate Similarity	NPD4821	Approved
0.7317	Intermediate Similarity	NPD7145	Approved
0.7317	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7143	Approved
0.7308	Intermediate Similarity	NPD7144	Approved
0.7294	Intermediate Similarity	NPD6695	Phase 3
0.7284	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6902	Approved
0.725	Intermediate Similarity	NPD4785	Approved
0.725	Intermediate Similarity	NPD4784	Approved
0.7215	Intermediate Similarity	NPD7151	Approved
0.7215	Intermediate Similarity	NPD7152	Approved
0.7215	Intermediate Similarity	NPD4243	Approved
0.7215	Intermediate Similarity	NPD7150	Approved
0.7209	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6932	Approved
0.7195	Intermediate Similarity	NPD6925	Approved
0.7195	Intermediate Similarity	NPD5776	Phase 2
0.7179	Intermediate Similarity	NPD6922	Approved
0.7179	Intermediate Similarity	NPD6923	Approved
0.716	Intermediate Similarity	NPD6942	Approved
0.716	Intermediate Similarity	NPD7339	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7126	Intermediate Similarity	NPD6893	Approved
0.7126	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4268	Approved
0.7108	Intermediate Similarity	NPD4271	Approved
0.6977	Remote Similarity	NPD4270	Approved
0.6977	Remote Similarity	NPD4269	Approved
0.6966	Remote Similarity	NPD7750	Discontinued
0.6966	Remote Similarity	NPD7524	Approved
0.6951	Remote Similarity	NPD8264	Approved
0.6941	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7509	Discontinued
0.6933	Remote Similarity	NPD368	Approved
0.686	Remote Similarity	NPD6898	Phase 1
0.6824	Remote Similarity	NPD6683	Phase 2
0.6824	Remote Similarity	NPD4195	Approved
0.6747	Remote Similarity	NPD4190	Phase 3
0.6747	Remote Similarity	NPD5275	Approved
0.6744	Remote Similarity	NPD4748	Discontinued
0.6744	Remote Similarity	NPD4252	Approved
0.6742	Remote Similarity	NPD5363	Approved
0.6739	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5369	Approved
0.6629	Remote Similarity	NPD3665	Phase 1
0.6629	Remote Similarity	NPD3666	Approved
0.6629	Remote Similarity	NPD3133	Approved
0.6629	Remote Similarity	NPD4786	Approved
0.6593	Remote Similarity	NPD4251	Approved
0.6593	Remote Similarity	NPD4250	Approved
0.6575	Remote Similarity	NPD342	Phase 1
0.6552	Remote Similarity	NPD5368	Approved
0.6517	Remote Similarity	NPD7154	Phase 3
0.6489	Remote Similarity	NPD7637	Suspended
0.6484	Remote Similarity	NPD4249	Approved
0.6452	Remote Similarity	NPD4753	Phase 2
0.6452	Remote Similarity	NPD6051	Approved
0.6444	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4202	Approved
0.6404	Remote Similarity	NPD4221	Approved
0.6404	Remote Similarity	NPD3667	Approved
0.6404	Remote Similarity	NPD4223	Phase 3
0.6404	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6374	Remote Similarity	NPD5329	Approved
0.6333	Remote Similarity	NPD4788	Approved
0.6316	Remote Similarity	NPD6079	Approved
0.631	Remote Similarity	NPD4732	Discontinued
0.6304	Remote Similarity	NPD5279	Phase 3
0.6304	Remote Similarity	NPD5690	Phase 2
0.6289	Remote Similarity	NPD4629	Approved
0.6289	Remote Similarity	NPD5210	Approved
0.6277	Remote Similarity	NPD5328	Approved
0.6275	Remote Similarity	NPD5141	Approved
0.6267	Remote Similarity	NPD4219	Approved
0.6264	Remote Similarity	NPD4197	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.6211	Remote Similarity	NPD7136	Phase 2
0.62	Remote Similarity	NPD5286	Approved
0.62	Remote Similarity	NPD7640	Approved
0.62	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD4696	Approved
0.62	Remote Similarity	NPD7639	Approved
0.617	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD4518	Approved
0.6162	Remote Similarity	NPD6084	Phase 2
0.6162	Remote Similarity	NPD4755	Approved
0.6162	Remote Similarity	NPD6083	Phase 2
0.6139	Remote Similarity	NPD5223	Approved
0.6129	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD4693	Phase 3
0.6129	Remote Similarity	NPD4694	Approved
0.6129	Remote Similarity	NPD4689	Approved
0.6129	Remote Similarity	NPD5280	Approved
0.6129	Remote Similarity	NPD5205	Approved
0.6129	Remote Similarity	NPD4688	Approved
0.6129	Remote Similarity	NPD4138	Approved
0.6129	Remote Similarity	NPD4690	Approved
0.61	Remote Similarity	NPD7638	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD4633	Approved
0.6078	Remote Similarity	NPD5225	Approved
0.6078	Remote Similarity	NPD5224	Approved
0.6078	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4700	Approved
0.6019	Remote Similarity	NPD5174	Approved
0.6019	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD4723	Approved
0.6	Remote Similarity	NPD4722	Approved
0.5979	Remote Similarity	NPD5281	Approved
0.5979	Remote Similarity	NPD5284	Approved
0.596	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD6409	Approved
0.5957	Remote Similarity	NPD4623	Approved
0.5957	Remote Similarity	NPD4519	Discontinued
0.5957	Remote Similarity	NPD7334	Approved
0.5957	Remote Similarity	NPD5330	Approved
0.5957	Remote Similarity	NPD7521	Approved
0.5957	Remote Similarity	NPD6684	Approved
0.5957	Remote Similarity	NPD7146	Approved
0.5943	Remote Similarity	NPD6899	Approved
0.5943	Remote Similarity	NPD6881	Approved
0.5934	Remote Similarity	NPD4139	Approved
0.5934	Remote Similarity	NPD4692	Approved
0.5918	Remote Similarity	NPD6399	Phase 3
0.5905	Remote Similarity	NPD5739	Approved
0.5905	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD6402	Approved
0.5905	Remote Similarity	NPD6675	Approved
0.59	Remote Similarity	NPD5221	Approved
0.59	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5222	Approved
0.59	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4787	Phase 1
0.5876	Remote Similarity	NPD4096	Approved
0.5872	Remote Similarity	NPD6053	Discontinued
0.5865	Remote Similarity	NPD4754	Approved
0.5851	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5697	Approved
0.5842	Remote Similarity	NPD5173	Approved
0.5833	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD7102	Approved
0.5833	Remote Similarity	NPD6883	Approved
0.5833	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6371	Approved
0.5794	Remote Similarity	NPD4730	Approved
0.5794	Remote Similarity	NPD6011	Approved
0.5794	Remote Similarity	NPD4729	Approved
0.5789	Remote Similarity	NPD6098	Approved
0.5784	Remote Similarity	NPD5696	Approved
0.578	Remote Similarity	NPD6650	Approved
0.578	Remote Similarity	NPD6869	Approved
0.578	Remote Similarity	NPD8130	Phase 1
0.578	Remote Similarity	NPD6847	Approved
0.578	Remote Similarity	NPD6649	Approved
0.578	Remote Similarity	NPD6617	Approved
0.5773	Remote Similarity	NPD5370	Suspended
0.5758	Remote Similarity	NPD5778	Approved
0.5758	Remote Similarity	NPD5779	Approved
0.5755	Remote Similarity	NPD4768	Approved
0.5755	Remote Similarity	NPD4767	Approved
0.5752	Remote Similarity	NPD7327	Approved
0.5752	Remote Similarity	NPD7328	Approved
0.575	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3668	Phase 3
0.5745	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4697	Phase 3
0.5741	Remote Similarity	NPD6012	Approved
0.5741	Remote Similarity	NPD6373	Approved
0.5741	Remote Similarity	NPD6013	Approved
0.5741	Remote Similarity	NPD6372	Approved
0.5741	Remote Similarity	NPD6014	Approved
0.5727	Remote Similarity	NPD8297	Approved
0.5727	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5702	Remote Similarity	NPD7516	Approved
0.5701	Remote Similarity	NPD5701	Approved
0.57	Remote Similarity	NPD5282	Discontinued

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