NPASS Compound

Structure

CID261372 OpenBabel06191716062D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.9616 3.1329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4665 0.7011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5916 -1.6388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5233 1.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9144 2.7715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 2.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7234 1.3702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4094 -1.0632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2452 2.0283 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8279 2.3647 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7452 1.1623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4243 -0.0633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3799 0.2314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3557 -1.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6939 2.8647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6504 -2.3420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9555 -0.5863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 4 7 1 0 0 0 0 4 12 1 0 0 0 0 5 11 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 8 2 1 6 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 3 1 6 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 5 1 1 0 0 0 10 14 1 0 0 0 0 11 23 1 1 0 0 0 12 15 1 0 0 0 0 12 28 1 6 0 0 0 13 6 1 1 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.2
Volume:	411.385
LogP:	-0.053
LogD:	0.925
LogS:	-1.886
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	5.181
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.04
MDCK Permeability:	0.0001202245766762644
Pgp-inhibitor:	0.006
Pgp-substrate:	0.637
Human Intestinal Absorption (HIA):	0.849
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	38.0230598449707%
Volume Distribution (VD):	0.451
Pgp-substrate:	57.833587646484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	2.332
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.454
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.066
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.737

Download Data

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

Natural Product: NPC261372

Natural Product ID:	NPC261372
*Common Name:**	(3S,3Ar,4S,6Ar,8S,9S,9Ar,9Br)-8-Hydroxy-3,9-Dimethyl-6-Methylidene-4-[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-3,3A,4,5,6A,7,8,9,9A,9B-Decahydroazuleno[4,5-B]Furan-2-One
IUPAC Name:	(3S,3aR,4S,6aR,8S,9S,9aR,9bR)-8-hydroxy-3,9-dimethyl-6-methylidene-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,4,5,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	BOYYQYRAKVYWCI-WCRLOTECSA-N
Standard InCHI:	InChI=1S/C21H32O9/c1-7-4-12(28-21-18(26)17(25)16(24)13(6-22)29-21)15-9(3)20(27)30-19(15)14-8(2)11(23)5-10(7)14/h8-19,21-26H,1,4-6H2,2-3H3/t8-,9+,10+,11+,12+,13-,14+,15-,16-,17+,18-,19-,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC(=C)[C@H]3[C@@H]([C@@H]4[C@@H]2[C@H](C)C(=O)O4)[C@@H]([C@H](C3)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1886093
PubChem CID:	44144277
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides 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
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18861	Pyxine coccifera	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18273	Merendera sobolifera	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16819	Preussia aemulans	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14834	Trachelospermum asiaticum	Species	Apocynaceae	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
Potency	5

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[473993]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	2059.6	nM	PMID[473993]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	5.2	nM	PMID[473993]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	18887.6	nM	PMID[473993]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[473993]

☑ 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 NPC261372 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	231
0.1-0.2	1755
0.2-0.3	6724
0.3-0.4	14452
0.4-0.5	8039
0.5-0.6	7162
0.6-0.7	3869
0.7-0.8	425
0.8-0.85	25
0.85-0.9	5
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC58267
1.0	High Similarity	NPC263674
0.9457	High Similarity	NPC474297
0.9355	High Similarity	NPC304445
0.9355	High Similarity	NPC236580
0.9072	High Similarity	NPC473148
0.9062	High Similarity	NPC67296
0.9053	High Similarity	NPC249171
0.9053	High Similarity	NPC49833
0.8958	High Similarity	NPC473146
0.8776	High Similarity	NPC80144
0.8737	High Similarity	NPC167893
0.8696	High Similarity	NPC470009
0.8617	High Similarity	NPC235051
0.8556	High Similarity	NPC111409
0.85	High Similarity	NPC475928
0.8469	Intermediate Similarity	NPC37866
0.8333	Intermediate Similarity	NPC170432
0.8333	Intermediate Similarity	NPC127235
0.83	Intermediate Similarity	NPC3488
0.83	Intermediate Similarity	NPC287539
0.8252	Intermediate Similarity	NPC148270
0.8252	Intermediate Similarity	NPC197813
0.8252	Intermediate Similarity	NPC80338
0.8218	Intermediate Similarity	NPC35185
0.8218	Intermediate Similarity	NPC4899
0.8218	Intermediate Similarity	NPC474730
0.8218	Intermediate Similarity	NPC177013
0.819	Intermediate Similarity	NPC106760
0.8163	Intermediate Similarity	NPC6765
0.8163	Intermediate Similarity	NPC93869
0.8163	Intermediate Similarity	NPC472873
0.8152	Intermediate Similarity	NPC128246
0.8144	Intermediate Similarity	NPC475788
0.8137	Intermediate Similarity	NPC37240
0.8061	Intermediate Similarity	NPC274588
0.8039	Intermediate Similarity	NPC106668
0.8039	Intermediate Similarity	NPC94919
0.8022	Intermediate Similarity	NPC258965
0.8022	Intermediate Similarity	NPC156658
0.8021	Intermediate Similarity	NPC215556
0.8019	Intermediate Similarity	NPC27551
0.8019	Intermediate Similarity	NPC114961
0.8019	Intermediate Similarity	NPC193741
0.8	Intermediate Similarity	NPC475773
0.8	Intermediate Similarity	NPC110701
0.8	Intermediate Similarity	NPC471150
0.8	Intermediate Similarity	NPC224414
0.7963	Intermediate Similarity	NPC102619
0.7961	Intermediate Similarity	NPC27687
0.7938	Intermediate Similarity	NPC54065
0.7938	Intermediate Similarity	NPC297474
0.7938	Intermediate Similarity	NPC216284
0.7935	Intermediate Similarity	NPC126248
0.7921	Intermediate Similarity	NPC472015
0.7917	Intermediate Similarity	NPC207114
0.7917	Intermediate Similarity	NPC217983
0.7917	Intermediate Similarity	NPC79549
0.79	Intermediate Similarity	NPC54731
0.79	Intermediate Similarity	NPC170527
0.79	Intermediate Similarity	NPC161293
0.7895	Intermediate Similarity	NPC470657
0.7879	Intermediate Similarity	NPC63897
0.787	Intermediate Similarity	NPC243572
0.787	Intermediate Similarity	NPC475924
0.787	Intermediate Similarity	NPC475851
0.7857	Intermediate Similarity	NPC472197
0.7857	Intermediate Similarity	NPC171360
0.7857	Intermediate Similarity	NPC63193
0.7857	Intermediate Similarity	NPC133888
0.7857	Intermediate Similarity	NPC29821
0.7857	Intermediate Similarity	NPC35959
0.7857	Intermediate Similarity	NPC293001
0.7857	Intermediate Similarity	NPC57304
0.7843	Intermediate Similarity	NPC471381
0.7843	Intermediate Similarity	NPC186861
0.7835	Intermediate Similarity	NPC155935
0.7822	Intermediate Similarity	NPC472290
0.7822	Intermediate Similarity	NPC474313
0.7818	Intermediate Similarity	NPC277583
0.7812	Intermediate Similarity	NPC31349
0.7798	Intermediate Similarity	NPC73455
0.7798	Intermediate Similarity	NPC200944
0.7778	Intermediate Similarity	NPC272242
0.7767	Intermediate Similarity	NPC216911
0.7757	Intermediate Similarity	NPC118225
0.7755	Intermediate Similarity	NPC35809
0.7755	Intermediate Similarity	NPC19087
0.7745	Intermediate Similarity	NPC45125
0.7736	Intermediate Similarity	NPC293512
0.7736	Intermediate Similarity	NPC287269
0.7708	Intermediate Similarity	NPC187661
0.7692	Intermediate Similarity	NPC70996
0.7692	Intermediate Similarity	NPC304163
0.7677	Intermediate Similarity	NPC475925
0.7677	Intermediate Similarity	NPC184063
0.7677	Intermediate Similarity	NPC155215
0.767	Intermediate Similarity	NPC476320
0.767	Intermediate Similarity	NPC476211
0.7664	Intermediate Similarity	NPC295389
0.7664	Intermediate Similarity	NPC88744
0.7653	Intermediate Similarity	NPC283409
0.7653	Intermediate Similarity	NPC38392
0.7653	Intermediate Similarity	NPC50464
0.7652	Intermediate Similarity	NPC256983
0.7647	Intermediate Similarity	NPC86843
0.7647	Intermediate Similarity	NPC181151
0.7647	Intermediate Similarity	NPC476612
0.7647	Intermediate Similarity	NPC476613
0.7647	Intermediate Similarity	NPC311904
0.7642	Intermediate Similarity	NPC54737
0.7642	Intermediate Similarity	NPC44004
0.7634	Intermediate Similarity	NPC51507
0.7624	Intermediate Similarity	NPC163228
0.7619	Intermediate Similarity	NPC329834
0.7615	Intermediate Similarity	NPC471251
0.7611	Intermediate Similarity	NPC161738
0.7604	Intermediate Similarity	NPC284534
0.7604	Intermediate Similarity	NPC204105
0.7604	Intermediate Similarity	NPC300082
0.76	Intermediate Similarity	NPC258216
0.76	Intermediate Similarity	NPC470187
0.7596	Intermediate Similarity	NPC476230
0.7596	Intermediate Similarity	NPC27474
0.7593	Intermediate Similarity	NPC91583
0.7593	Intermediate Similarity	NPC139838
0.7593	Intermediate Similarity	NPC240125
0.7593	Intermediate Similarity	NPC59489
0.7593	Intermediate Similarity	NPC473844
0.7593	Intermediate Similarity	NPC51947
0.7589	Intermediate Similarity	NPC156651
0.7579	Intermediate Similarity	NPC474266
0.7576	Intermediate Similarity	NPC206614
0.7576	Intermediate Similarity	NPC246173
0.7576	Intermediate Similarity	NPC474323
0.7551	Intermediate Similarity	NPC471149
0.7549	Intermediate Similarity	NPC18019
0.7549	Intermediate Similarity	NPC306041
0.7549	Intermediate Similarity	NPC24956
0.7549	Intermediate Similarity	NPC91771
0.7549	Intermediate Similarity	NPC284063
0.7549	Intermediate Similarity	NPC142529
0.7547	Intermediate Similarity	NPC223741
0.7547	Intermediate Similarity	NPC121566
0.7547	Intermediate Similarity	NPC100955
0.7545	Intermediate Similarity	NPC233003
0.7545	Intermediate Similarity	NPC470543
0.7544	Intermediate Similarity	NPC142882
0.7544	Intermediate Similarity	NPC471406
0.7526	Intermediate Similarity	NPC56593
0.7526	Intermediate Similarity	NPC304558
0.7525	Intermediate Similarity	NPC472198
0.7523	Intermediate Similarity	NPC127153
0.7523	Intermediate Similarity	NPC129340
0.7523	Intermediate Similarity	NPC101450
0.7521	Intermediate Similarity	NPC47113
0.7521	Intermediate Similarity	NPC174367
0.7521	Intermediate Similarity	NPC273962
0.75	Intermediate Similarity	NPC88945
0.75	Intermediate Similarity	NPC472199
0.75	Intermediate Similarity	NPC66504
0.75	Intermediate Similarity	NPC224386
0.75	Intermediate Similarity	NPC68248
0.75	Intermediate Similarity	NPC194859
0.75	Intermediate Similarity	NPC195708
0.7478	Intermediate Similarity	NPC473228
0.7478	Intermediate Similarity	NPC470829
0.7478	Intermediate Similarity	NPC182900
0.7478	Intermediate Similarity	NPC249553
0.7477	Intermediate Similarity	NPC95243
0.7477	Intermediate Similarity	NPC477944
0.7477	Intermediate Similarity	NPC210178
0.7477	Intermediate Similarity	NPC63023
0.7477	Intermediate Similarity	NPC162033
0.7477	Intermediate Similarity	NPC251309
0.7476	Intermediate Similarity	NPC161493
0.7475	Intermediate Similarity	NPC92974
0.7475	Intermediate Similarity	NPC472872
0.7474	Intermediate Similarity	NPC475849
0.7474	Intermediate Similarity	NPC246076
0.7456	Intermediate Similarity	NPC477071
0.7455	Intermediate Similarity	NPC263827
0.7455	Intermediate Similarity	NPC275668
0.7455	Intermediate Similarity	NPC250481
0.7455	Intermediate Similarity	NPC91838
0.7455	Intermediate Similarity	NPC285410
0.7455	Intermediate Similarity	NPC240734
0.7455	Intermediate Similarity	NPC1876
0.7455	Intermediate Similarity	NPC11035
0.7455	Intermediate Similarity	NPC204392
0.7453	Intermediate Similarity	NPC329704
0.7451	Intermediate Similarity	NPC52044
0.7451	Intermediate Similarity	NPC215570
0.7451	Intermediate Similarity	NPC213698
0.7451	Intermediate Similarity	NPC476053
0.7451	Intermediate Similarity	NPC67584
0.7449	Intermediate Similarity	NPC24728
0.7449	Intermediate Similarity	NPC265580
0.7434	Intermediate Similarity	NPC473304
0.7431	Intermediate Similarity	NPC477070

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 NPC261372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	2458
0.2-0.3	4037
0.3-0.4	1594
0.4-0.5	445
0.5-0.6	305
0.6-0.7	83
0.7-0.8	1
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
0.7407	Intermediate Similarity	NPD6412	Phase 2
0.7407	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8133	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD46	Approved
0.6991	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4251	Approved
0.6931	Remote Similarity	NPD4250	Approved
0.6911	Remote Similarity	NPD7319	Approved
0.6909	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6371	Approved
0.6869	Remote Similarity	NPD5362	Discontinued
0.6832	Remote Similarity	NPD4249	Approved
0.6814	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1695	Approved
0.678	Remote Similarity	NPD7327	Approved
0.678	Remote Similarity	NPD7328	Approved
0.6768	Remote Similarity	NPD6435	Approved
0.675	Remote Similarity	NPD8517	Approved
0.675	Remote Similarity	NPD8033	Approved
0.675	Remote Similarity	NPD8515	Approved
0.675	Remote Similarity	NPD8513	Phase 3
0.675	Remote Similarity	NPD8516	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6723	Remote Similarity	NPD7516	Approved
0.6701	Remote Similarity	NPD4238	Approved
0.6701	Remote Similarity	NPD4802	Phase 2
0.6694	Remote Similarity	NPD6370	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6638	Remote Similarity	NPD6053	Discontinued
0.6612	Remote Similarity	NPD8378	Approved
0.6612	Remote Similarity	NPD8296	Approved
0.6612	Remote Similarity	NPD8380	Approved
0.6612	Remote Similarity	NPD8335	Approved
0.6612	Remote Similarity	NPD8379	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6569	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5368	Approved
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6616	Approved
0.6529	Remote Similarity	NPD6054	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.65	Remote Similarity	NPD7641	Discontinued
0.648	Remote Similarity	NPD7078	Approved
0.6475	Remote Similarity	NPD7503	Approved
0.6455	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8171	Discontinued
0.6449	Remote Similarity	NPD6399	Phase 3
0.6436	Remote Similarity	NPD4270	Approved
0.6436	Remote Similarity	NPD4269	Approved
0.6417	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4819	Approved
0.64	Remote Similarity	NPD4822	Approved
0.64	Remote Similarity	NPD4820	Approved
0.64	Remote Similarity	NPD4821	Approved
0.6389	Remote Similarity	NPD5282	Discontinued
0.6373	Remote Similarity	NPD5331	Approved
0.6373	Remote Similarity	NPD7154	Phase 3
0.6373	Remote Similarity	NPD5332	Approved
0.6371	Remote Similarity	NPD6067	Discontinued
0.6371	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6356	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD8034	Phase 2
0.6355	Remote Similarity	NPD8035	Phase 2
0.6346	Remote Similarity	NPD5786	Approved
0.6341	Remote Similarity	NPD6015	Approved
0.6341	Remote Similarity	NPD8268	Approved
0.6341	Remote Similarity	NPD8269	Approved
0.6341	Remote Similarity	NPD8266	Approved
0.6341	Remote Similarity	NPD8267	Approved
0.6341	Remote Similarity	NPD6016	Approved
0.6337	Remote Similarity	NPD4790	Discontinued
0.633	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5988	Approved
0.6281	Remote Similarity	NPD6009	Approved
0.6273	Remote Similarity	NPD7839	Suspended
0.6262	Remote Similarity	NPD7838	Discovery
0.6261	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD5363	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6238	Remote Similarity	NPD4252	Approved
0.622	Remote Similarity	NPD8074	Phase 3
0.6218	Remote Similarity	NPD8297	Approved
0.6216	Remote Similarity	NPD6083	Phase 2
0.6216	Remote Similarity	NPD6084	Phase 2
0.6214	Remote Similarity	NPD3669	Approved
0.6214	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8341	Approved
0.619	Remote Similarity	NPD8299	Approved
0.619	Remote Similarity	NPD8342	Approved
0.619	Remote Similarity	NPD8340	Approved
0.6172	Remote Similarity	NPD8336	Approved
0.6172	Remote Similarity	NPD8337	Approved
0.6168	Remote Similarity	NPD6101	Approved
0.6168	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4632	Approved
0.616	Remote Similarity	NPD8080	Discontinued
0.6154	Remote Similarity	NPD7320	Approved
0.6147	Remote Similarity	NPD5779	Approved
0.6147	Remote Similarity	NPD5778	Approved
0.6142	Remote Similarity	NPD8451	Approved
0.614	Remote Similarity	NPD8138	Approved
0.614	Remote Similarity	NPD8083	Approved
0.614	Remote Similarity	NPD8086	Approved
0.614	Remote Similarity	NPD8082	Approved
0.614	Remote Similarity	NPD8139	Approved
0.614	Remote Similarity	NPD8085	Approved
0.614	Remote Similarity	NPD8084	Approved
0.6134	Remote Similarity	NPD6650	Approved
0.6134	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD5739	Approved
0.6121	Remote Similarity	NPD6402	Approved
0.6121	Remote Similarity	NPD7128	Approved
0.6121	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD3198	Approved
0.6111	Remote Similarity	NPD5785	Approved
0.6095	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD8448	Approved
0.6087	Remote Similarity	NPD8275	Approved
0.6087	Remote Similarity	NPD8276	Approved
0.608	Remote Similarity	NPD8444	Approved
0.6055	Remote Similarity	NPD6411	Approved
0.6055	Remote Similarity	NPD7637	Suspended
0.6047	Remote Similarity	NPD6033	Approved
0.604	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5695	Phase 3
0.6034	Remote Similarity	NPD8081	Approved
0.6019	Remote Similarity	NPD1780	Approved
0.6019	Remote Similarity	NPD1779	Approved
0.6018	Remote Similarity	NPD5696	Approved
0.6018	Remote Similarity	NPD7638	Approved
0.6017	Remote Similarity	NPD6899	Approved
0.6017	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6881	Approved
0.5985	Remote Similarity	NPD8338	Approved
0.5984	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD7642	Approved
0.5984	Remote Similarity	NPD7122	Discontinued
0.5984	Remote Similarity	NPD7829	Approved
0.5983	Remote Similarity	NPD8393	Approved
0.5981	Remote Similarity	NPD7524	Approved
0.5979	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7640	Approved
0.5965	Remote Similarity	NPD7639	Approved
0.5954	Remote Similarity	NPD5956	Approved
0.5954	Remote Similarity	NPD8390	Approved
0.5954	Remote Similarity	NPD8392	Approved
0.5954	Remote Similarity	NPD8391	Approved
0.5943	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6940	Discontinued
0.5932	Remote Similarity	NPD5701	Approved
0.5932	Remote Similarity	NPD6685	Approved
0.5932	Remote Similarity	NPD5697	Approved
0.5926	Remote Similarity	NPD6903	Approved
0.5922	Remote Similarity	NPD6928	Phase 2
0.5917	Remote Similarity	NPD6883	Approved
0.5917	Remote Similarity	NPD7102	Approved
0.5917	Remote Similarity	NPD7290	Approved
0.5913	Remote Similarity	NPD1700	Approved
0.5905	Remote Similarity	NPD4788	Approved
0.5893	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7521	Approved
0.5888	Remote Similarity	NPD6409	Approved
0.5888	Remote Similarity	NPD7146	Approved
0.5888	Remote Similarity	NPD7334	Approved
0.5888	Remote Similarity	NPD5330	Approved
0.5888	Remote Similarity	NPD6684	Approved
0.5887	Remote Similarity	NPD7115	Discovery
0.5877	Remote Similarity	NPD4225	Approved
0.5868	Remote Similarity	NPD8130	Phase 1
0.5868	Remote Similarity	NPD6847	Approved
0.5868	Remote Similarity	NPD6617	Approved
0.5868	Remote Similarity	NPD6869	Approved
0.5865	Remote Similarity	NPD8449	Approved
0.5859	Remote Similarity	NPD7604	Phase 2
0.5851	Remote Similarity	NPD7909	Approved
0.5849	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD896	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD898	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5833	Remote Similarity	NPD897	Approved
0.5827	Remote Similarity	NPD5983	Phase 2
0.5821	Remote Similarity	NPD8450	Suspended

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