NPASS Compound

Structure

NPC187761 OpenBabel07101718282D 27 28 0 0 1 0 0 0 0 0999 V2000 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 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 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 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 -3.4641 -2.0000 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 -1.7321 -2.0000 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 1 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 2 1 1 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 3 1 6 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 4 1 1 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 14 21 1 6 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 25 1 6 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 18 20 1 6 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 5 1 6 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.21
Volume:	390.985
LogP:	2.526
LogD:	2.485
LogS:	-3.346
# Rotatable Bonds:	8
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	4.554
Fsp3:	0.85
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:	-4.686
MDCK Permeability:	4.6227236452978104e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.237
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.805
Plasma Protein Binding (PPB):	52.536964416503906%
Volume Distribution (VD):	0.733
Pgp-substrate:	45.56464767456055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.418
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	9.664
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.93
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.334
Carcinogencity:	0.054
Eye Corrosion:	0.012
Eye Irritation:	0.015
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC187761

Natural Product ID:	NPC187761
*Common Name:**	3-O-Deacetylbotcinin A
IUPAC Name:	[(2S,3R,4R,4aS,7R,8S,8aR)-8-hydroxy-2,4,7,8a-tetramethyl-6-oxo-2,3,4,4a,7,8-hexahydropyrano[3,2-b]pyran-3-yl] (E,4S)-4-hydroxyoct-2-enoate
Synonyms:
Standard InCHIKey:	NTXBEGLMBLTXSP-OSOLHDLVSA-N
Standard InCHI:	InChI=1S/C20H32O7/c1-6-7-8-14(21)9-10-15(22)25-16-11(2)18-20(5,27-13(16)4)17(23)12(3)19(24)26-18/h9-14,16-18,21,23H,6-8H2,1-5H3/b10-9+/t11-,12-,13+,14+,16-,17+,18+,20-/m1/s1
SMILES:	CCCC[C@@H](/C=C/C(=O)O[C@H]1[C@H](C)O[C@]2([C@H]([C@@H]1C)OC(=O)[C@@H]([C@@H]2O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496053
PubChem CID:	11567174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	100000.0	nM	PMID[523933]

☑ 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 NPC187761 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	206
0.1-0.2	1150
0.2-0.3	3892
0.3-0.4	6743
0.4-0.5	12763
0.5-0.6	9863
0.6-0.7	6313
0.7-0.8	1692
0.8-0.85	64
0.85-0.9	5
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC83895
0.9783	High Similarity	NPC261377
0.9783	High Similarity	NPC255592
0.9783	High Similarity	NPC308567
0.9674	High Similarity	NPC40812
0.8737	High Similarity	NPC71589
0.8646	High Similarity	NPC36954
0.8632	High Similarity	NPC475912
0.8526	High Similarity	NPC470379
0.8526	High Similarity	NPC30515
0.8526	High Similarity	NPC184463
0.8526	High Similarity	NPC470373
0.8485	Intermediate Similarity	NPC288876
0.8478	Intermediate Similarity	NPC137033
0.8454	Intermediate Similarity	NPC270013
0.8454	Intermediate Similarity	NPC14961
0.8438	Intermediate Similarity	NPC476300
0.8431	Intermediate Similarity	NPC476738
0.8431	Intermediate Similarity	NPC476740
0.8421	Intermediate Similarity	NPC474761
0.8421	Intermediate Similarity	NPC51004
0.8421	Intermediate Similarity	NPC473448
0.8421	Intermediate Similarity	NPC476004
0.8416	Intermediate Similarity	NPC309398
0.8416	Intermediate Similarity	NPC475945
0.8416	Intermediate Similarity	NPC475871
0.8404	Intermediate Similarity	NPC227379
0.8404	Intermediate Similarity	NPC153805
0.8404	Intermediate Similarity	NPC474471
0.837	Intermediate Similarity	NPC9868
0.837	Intermediate Similarity	NPC70424
0.837	Intermediate Similarity	NPC243618
0.8367	Intermediate Similarity	NPC476315
0.8365	Intermediate Similarity	NPC315836
0.8365	Intermediate Similarity	NPC313668
0.8351	Intermediate Similarity	NPC474035
0.8351	Intermediate Similarity	NPC81386
0.8333	Intermediate Similarity	NPC100487
0.8317	Intermediate Similarity	NPC474747
0.8317	Intermediate Similarity	NPC149371
0.8317	Intermediate Similarity	NPC473596
0.8317	Intermediate Similarity	NPC313569
0.8316	Intermediate Similarity	NPC307411
0.83	Intermediate Similarity	NPC475053
0.8298	Intermediate Similarity	NPC248602
0.8283	Intermediate Similarity	NPC266842
0.8269	Intermediate Similarity	NPC193765
0.8265	Intermediate Similarity	NPC471142
0.8265	Intermediate Similarity	NPC272050
0.8261	Intermediate Similarity	NPC11620
0.8247	Intermediate Similarity	NPC81419
0.8247	Intermediate Similarity	NPC179746
0.8247	Intermediate Similarity	NPC212486
0.8235	Intermediate Similarity	NPC473816
0.8235	Intermediate Similarity	NPC472755
0.8235	Intermediate Similarity	NPC474581
0.8235	Intermediate Similarity	NPC475367
0.8235	Intermediate Similarity	NPC110989
0.8218	Intermediate Similarity	NPC472753
0.8218	Intermediate Similarity	NPC47880
0.8218	Intermediate Similarity	NPC474742
0.8211	Intermediate Similarity	NPC202672
0.82	Intermediate Similarity	NPC471144
0.8198	Intermediate Similarity	NPC470829
0.8198	Intermediate Similarity	NPC473228
0.8191	Intermediate Similarity	NPC164393
0.8182	Intermediate Similarity	NPC477921
0.8182	Intermediate Similarity	NPC473859
0.8155	Intermediate Similarity	NPC203659
0.8155	Intermediate Similarity	NPC474741
0.8144	Intermediate Similarity	NPC208886
0.8144	Intermediate Similarity	NPC473321
0.8144	Intermediate Similarity	NPC12172
0.8137	Intermediate Similarity	NPC472754
0.8137	Intermediate Similarity	NPC225353
0.8113	Intermediate Similarity	NPC5103
0.8095	Intermediate Similarity	NPC473807
0.8095	Intermediate Similarity	NPC475960
0.8091	Intermediate Similarity	NPC13710
0.8091	Intermediate Similarity	NPC475309
0.8081	Intermediate Similarity	NPC477922
0.8081	Intermediate Similarity	NPC475659
0.8077	Intermediate Similarity	NPC472749
0.8077	Intermediate Similarity	NPC472751
0.8061	Intermediate Similarity	NPC273579
0.8061	Intermediate Similarity	NPC162205
0.8061	Intermediate Similarity	NPC288240
0.8061	Intermediate Similarity	NPC295204
0.8061	Intermediate Similarity	NPC476049
0.8058	Intermediate Similarity	NPC472747
0.8058	Intermediate Similarity	NPC472750
0.8056	Intermediate Similarity	NPC469496
0.8056	Intermediate Similarity	NPC469454
0.8056	Intermediate Similarity	NPC469463
0.8041	Intermediate Similarity	NPC473619
0.8041	Intermediate Similarity	NPC313670
0.8041	Intermediate Similarity	NPC475855
0.8041	Intermediate Similarity	NPC3952
0.8039	Intermediate Similarity	NPC46998
0.8039	Intermediate Similarity	NPC110443
0.8039	Intermediate Similarity	NPC185141
0.8039	Intermediate Similarity	NPC128733
0.8039	Intermediate Similarity	NPC133907
0.8021	Intermediate Similarity	NPC281516
0.802	Intermediate Similarity	NPC187268
0.802	Intermediate Similarity	NPC475653
0.802	Intermediate Similarity	NPC473326
0.802	Intermediate Similarity	NPC474213
0.8	Intermediate Similarity	NPC477513
0.8	Intermediate Similarity	NPC230800
0.8	Intermediate Similarity	NPC311163
0.8	Intermediate Similarity	NPC469483
0.8	Intermediate Similarity	NPC279621
0.7981	Intermediate Similarity	NPC220964
0.7981	Intermediate Similarity	NPC146731
0.7981	Intermediate Similarity	NPC472756
0.7981	Intermediate Similarity	NPC469869
0.7981	Intermediate Similarity	NPC475676
0.7981	Intermediate Similarity	NPC296950
0.7981	Intermediate Similarity	NPC472748
0.798	Intermediate Similarity	NPC57405
0.798	Intermediate Similarity	NPC303942
0.7979	Intermediate Similarity	NPC474780
0.7979	Intermediate Similarity	NPC72464
0.7963	Intermediate Similarity	NPC269530
0.7959	Intermediate Similarity	NPC329952
0.7959	Intermediate Similarity	NPC476705
0.7944	Intermediate Similarity	NPC41551
0.7938	Intermediate Similarity	NPC474032
0.7938	Intermediate Similarity	NPC133450
0.7938	Intermediate Similarity	NPC295312
0.7935	Intermediate Similarity	NPC233377
0.7921	Intermediate Similarity	NPC120299
0.7917	Intermediate Similarity	NPC86005
0.7912	Intermediate Similarity	NPC127526
0.7905	Intermediate Similarity	NPC243998
0.79	Intermediate Similarity	NPC304886
0.7895	Intermediate Similarity	NPC471494
0.7895	Intermediate Similarity	NPC21469
0.7895	Intermediate Similarity	NPC261380
0.7885	Intermediate Similarity	NPC475873
0.7885	Intermediate Similarity	NPC4620
0.7879	Intermediate Similarity	NPC469645
0.7879	Intermediate Similarity	NPC469692
0.7879	Intermediate Similarity	NPC475838
0.7879	Intermediate Similarity	NPC228451
0.7879	Intermediate Similarity	NPC125674
0.7872	Intermediate Similarity	NPC44261
0.7872	Intermediate Similarity	NPC69469
0.787	Intermediate Similarity	NPC304180
0.787	Intermediate Similarity	NPC179798
0.787	Intermediate Similarity	NPC317107
0.7864	Intermediate Similarity	NPC164598
0.7864	Intermediate Similarity	NPC201718
0.7864	Intermediate Similarity	NPC476270
0.7864	Intermediate Similarity	NPC474339
0.7857	Intermediate Similarity	NPC179394
0.7857	Intermediate Similarity	NPC144133
0.7857	Intermediate Similarity	NPC177668
0.7857	Intermediate Similarity	NPC475748
0.785	Intermediate Similarity	NPC38154
0.7843	Intermediate Similarity	NPC161855
0.7838	Intermediate Similarity	NPC471145
0.7838	Intermediate Similarity	NPC471146
0.7835	Intermediate Similarity	NPC473715
0.7835	Intermediate Similarity	NPC177629
0.7835	Intermediate Similarity	NPC58219
0.783	Intermediate Similarity	NPC254538
0.783	Intermediate Similarity	NPC474285
0.7822	Intermediate Similarity	NPC76862
0.7822	Intermediate Similarity	NPC158416
0.7822	Intermediate Similarity	NPC255410
0.7822	Intermediate Similarity	NPC470883
0.7822	Intermediate Similarity	NPC473291
0.7822	Intermediate Similarity	NPC39859
0.7812	Intermediate Similarity	NPC47937
0.7812	Intermediate Similarity	NPC122502
0.7812	Intermediate Similarity	NPC475019
0.7812	Intermediate Similarity	NPC474949
0.781	Intermediate Similarity	NPC470104
0.781	Intermediate Similarity	NPC309190
0.781	Intermediate Similarity	NPC239162
0.781	Intermediate Similarity	NPC474917
0.78	Intermediate Similarity	NPC474247
0.78	Intermediate Similarity	NPC121825
0.7798	Intermediate Similarity	NPC90952
0.7798	Intermediate Similarity	NPC317687
0.7798	Intermediate Similarity	NPC476801
0.7798	Intermediate Similarity	NPC66108
0.7789	Intermediate Similarity	NPC475963
0.7789	Intermediate Similarity	NPC3464
0.7789	Intermediate Similarity	NPC151176
0.7788	Intermediate Similarity	NPC86077
0.7788	Intermediate Similarity	NPC48692
0.7788	Intermediate Similarity	NPC320019
0.7788	Intermediate Similarity	NPC471148
0.7788	Intermediate Similarity	NPC324017
0.7778	Intermediate Similarity	NPC300312
0.7778	Intermediate Similarity	NPC235014
0.7778	Intermediate Similarity	NPC111114

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 NPC187761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1448
0.2-0.3	3542
0.3-0.4	2450
0.4-0.5	971
0.5-0.6	357
0.6-0.7	171
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8229	Intermediate Similarity	NPD6698	Approved
0.8229	Intermediate Similarity	NPD46	Approved
0.8144	Intermediate Similarity	NPD7983	Approved
0.802	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6371	Approved
0.7706	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5779	Approved
0.77	Intermediate Similarity	NPD5778	Approved
0.7677	Intermediate Similarity	NPD7838	Discovery
0.7664	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6686	Approved
0.7565	Intermediate Similarity	NPD8516	Approved
0.7565	Intermediate Similarity	NPD8513	Phase 3
0.7565	Intermediate Similarity	NPD8515	Approved
0.7565	Intermediate Similarity	NPD8517	Approved
0.7436	Intermediate Similarity	NPD7830	Approved
0.7436	Intermediate Similarity	NPD7829	Approved
0.7431	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5344	Discontinued
0.7333	Intermediate Similarity	NPD4225	Approved
0.7327	Intermediate Similarity	NPD5785	Approved
0.7311	Intermediate Similarity	NPD8451	Approved
0.7308	Intermediate Similarity	NPD7839	Suspended
0.7288	Intermediate Similarity	NPD7642	Approved
0.725	Intermediate Similarity	NPD8448	Approved
0.725	Intermediate Similarity	NPD8074	Phase 3
0.7228	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6101	Approved
0.7227	Intermediate Similarity	NPD8341	Approved
0.7227	Intermediate Similarity	NPD8342	Approved
0.7227	Intermediate Similarity	NPD8340	Approved
0.7227	Intermediate Similarity	NPD8299	Approved
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7172	Intermediate Similarity	NPD5363	Approved
0.7172	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5786	Approved
0.7087	Intermediate Similarity	NPD6411	Approved
0.7073	Intermediate Similarity	NPD8391	Approved
0.7073	Intermediate Similarity	NPD8392	Approved
0.7073	Intermediate Similarity	NPD8390	Approved
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.7008	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7319	Approved
0.6952	Remote Similarity	NPD5282	Discontinued
0.6944	Remote Similarity	NPD6648	Approved
0.6891	Remote Similarity	NPD6319	Approved
0.6885	Remote Similarity	NPD7507	Approved
0.6869	Remote Similarity	NPD4270	Approved
0.6869	Remote Similarity	NPD4269	Approved
0.6869	Remote Similarity	NPD6435	Approved
0.686	Remote Similarity	NPD8328	Phase 3
0.6833	Remote Similarity	NPD8444	Approved
0.68	Remote Similarity	NPD7154	Phase 3
0.6789	Remote Similarity	NPD7640	Approved
0.6789	Remote Similarity	NPD7639	Approved
0.6768	Remote Similarity	NPD5369	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8273	Phase 1
0.6723	Remote Similarity	NPD7641	Discontinued
0.6699	Remote Similarity	NPD4251	Approved
0.6699	Remote Similarity	NPD4250	Approved
0.6697	Remote Similarity	NPD7638	Approved
0.6694	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6634	Remote Similarity	NPD6110	Phase 1
0.6613	Remote Similarity	NPD6616	Approved
0.6612	Remote Similarity	NPD6054	Approved
0.6604	Remote Similarity	NPD7637	Suspended
0.6602	Remote Similarity	NPD4249	Approved
0.6581	Remote Similarity	NPD8297	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6571	Remote Similarity	NPD1695	Approved
0.656	Remote Similarity	NPD7078	Approved
0.6552	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6881	Approved
0.6522	Remote Similarity	NPD6899	Approved
0.6508	Remote Similarity	NPD7736	Approved
0.6505	Remote Similarity	NPD1694	Approved
0.6504	Remote Similarity	NPD6370	Approved
0.6504	Remote Similarity	NPD8080	Discontinued
0.65	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6649	Approved
0.6496	Remote Similarity	NPD6650	Approved
0.6484	Remote Similarity	NPD7260	Phase 2
0.6471	Remote Similarity	NPD5362	Discontinued
0.6465	Remote Similarity	NPD4271	Approved
0.6465	Remote Similarity	NPD4268	Approved
0.6465	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8415	Approved
0.6435	Remote Similarity	NPD5697	Approved
0.6423	Remote Similarity	NPD7503	Approved
0.6423	Remote Similarity	NPD6016	Approved
0.6423	Remote Similarity	NPD6015	Approved
0.641	Remote Similarity	NPD7290	Approved
0.641	Remote Similarity	NPD4634	Approved
0.641	Remote Similarity	NPD7102	Approved
0.641	Remote Similarity	NPD6883	Approved
0.6387	Remote Similarity	NPD8133	Approved
0.6371	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD7500	Approved
0.6364	Remote Similarity	NPD6009	Approved
0.6356	Remote Similarity	NPD6847	Approved
0.6356	Remote Similarity	NPD6617	Approved
0.6356	Remote Similarity	NPD6869	Approved
0.6356	Remote Similarity	NPD8130	Phase 1
0.6348	Remote Similarity	NPD7128	Approved
0.6348	Remote Similarity	NPD6675	Approved
0.6348	Remote Similarity	NPD5739	Approved
0.6348	Remote Similarity	NPD6402	Approved
0.6346	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8377	Approved
0.6341	Remote Similarity	NPD6059	Approved
0.6341	Remote Similarity	NPD8294	Approved
0.6325	Remote Similarity	NPD6012	Approved
0.6325	Remote Similarity	NPD6373	Approved
0.6325	Remote Similarity	NPD6013	Approved
0.6325	Remote Similarity	NPD6372	Approved
0.6325	Remote Similarity	NPD6014	Approved
0.632	Remote Similarity	NPD7604	Phase 2
0.6311	Remote Similarity	NPD7328	Approved
0.6311	Remote Similarity	NPD7327	Approved
0.6303	Remote Similarity	NPD6882	Approved
0.6299	Remote Similarity	NPD8293	Discontinued
0.6296	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8379	Approved
0.629	Remote Similarity	NPD8380	Approved
0.629	Remote Similarity	NPD8296	Approved
0.629	Remote Similarity	NPD8033	Approved
0.629	Remote Similarity	NPD8335	Approved
0.629	Remote Similarity	NPD8378	Approved
0.629	Remote Similarity	NPD5983	Phase 2
0.6277	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6421	Discontinued
0.6262	Remote Similarity	NPD5370	Suspended
0.626	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7320	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6228	Remote Similarity	NPD8083	Approved
0.6228	Remote Similarity	NPD8082	Approved
0.6228	Remote Similarity	NPD7632	Discontinued
0.6228	Remote Similarity	NPD5211	Phase 2
0.6228	Remote Similarity	NPD8139	Approved
0.6228	Remote Similarity	NPD8084	Approved
0.6228	Remote Similarity	NPD8138	Approved
0.6228	Remote Similarity	NPD8085	Approved
0.6228	Remote Similarity	NPD8086	Approved
0.622	Remote Similarity	NPD6336	Discontinued
0.6214	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5209	Approved
0.6207	Remote Similarity	NPD5048	Discontinued
0.6186	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8276	Approved
0.6174	Remote Similarity	NPD8275	Approved
0.617	Remote Similarity	NPD7331	Phase 2
0.6162	Remote Similarity	NPD8039	Approved
0.6161	Remote Similarity	NPD6084	Phase 2
0.6161	Remote Similarity	NPD7902	Approved
0.6161	Remote Similarity	NPD6083	Phase 2
0.616	Remote Similarity	NPD8267	Approved
0.616	Remote Similarity	NPD8268	Approved
0.616	Remote Similarity	NPD8266	Approved
0.616	Remote Similarity	NPD8269	Approved
0.6154	Remote Similarity	NPD5701	Approved
0.6132	Remote Similarity	NPD6422	Discontinued
0.6129	Remote Similarity	NPD3197	Phase 1
0.6121	Remote Similarity	NPD8081	Approved
0.6121	Remote Similarity	NPD5141	Approved
0.6091	Remote Similarity	NPD6399	Phase 3
0.6083	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3573	Approved
0.6075	Remote Similarity	NPD7524	Approved
0.6068	Remote Similarity	NPD8393	Approved
0.6068	Remote Similarity	NPD6008	Approved
0.6064	Remote Similarity	NPD7341	Phase 2
0.6064	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6845	Suspended
0.6053	Remote Similarity	NPD5285	Approved
0.6053	Remote Similarity	NPD5286	Approved
0.6053	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD7748	Approved
0.6014	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD5331	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