NPASS Compound

Structure

NPC35717 OpenBabel07101718252D 21 23 0 0 1 0 0 0 0 0999 V2000 1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 -1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 6 0 0 0 11 18 2 0 0 0 0 12 16 1 6 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 9 1 6 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.15
Volume:	295.665
LogP:	1.574
LogD:	1.707
LogS:	-2.613
# Rotatable Bonds:	1
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.761
Synthetic Accessibility Score:	4.781
Fsp3:	0.688
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:	-4.702
MDCK Permeability:	2.6584952138364315e-05
Pgp-inhibitor:	0.151
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.395
Plasma Protein Binding (PPB):	76.58494567871094%
Volume Distribution (VD):	1.222
Pgp-substrate:	21.16714096069336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.16
CYP2C19-substrate:	0.67
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	7.629
Half-life (T1/2):	0.557

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.105
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.813
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.198
Carcinogencity:	0.867
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.807

Download Data

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

Natural Product: NPC35717

Natural Product ID:	NPC35717
*Common Name:**	Pestaloficiol I
IUPAC Name:	(6S,6aR,8S)-6-hydroxy-8-(2-hydroxypropan-2-yl)-2,2-dimethyl-5,6,6a,8-tetrahydro-3H-furo[2,3-h]chromen-4-one
Synonyms:	Pestaloficiol I
Standard InCHIKey:	JYXSZFDEOPSZCU-VHRBIJSZSA-N
Standard InCHI:	InChI=1S/C16H22O5/c1-15(2)7-11(18)8-5-10(17)14-9(13(8)21-15)6-12(20-14)16(3,4)19/h6,10,12,14,17,19H,5,7H2,1-4H3/t10-,12-,14+/m0/s1
SMILES:	CC1(C)CC(=O)C2=C(C3=C[C@@H](C(C)(C)O)O[C@H]3[C@H](C2)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080257
PubChem CID:	44254250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	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
EC50	1
IC50	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	136100.0	nM	PMID[558465]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	136100.0	nM	PMID[558465]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[558465]

☑ 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 NPC35717 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	202
0.1-0.2	1149
0.2-0.3	4213
0.3-0.4	8305
0.4-0.5	16564
0.5-0.6	8720
0.6-0.7	3152
0.7-0.8	370
0.8-0.85	16
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9158	High Similarity	NPC306908
0.8817	High Similarity	NPC469464
0.8351	Intermediate Similarity	NPC477241
0.8283	Intermediate Similarity	NPC239895
0.8252	Intermediate Similarity	NPC469852
0.8173	Intermediate Similarity	NPC469853
0.8065	Intermediate Similarity	NPC185256
0.7959	Intermediate Similarity	NPC146852
0.7959	Intermediate Similarity	NPC327760
0.7921	Intermediate Similarity	NPC20066
0.7895	Intermediate Similarity	NPC68303
0.7895	Intermediate Similarity	NPC307126
0.7879	Intermediate Similarity	NPC61275
0.7864	Intermediate Similarity	NPC469851
0.7864	Intermediate Similarity	NPC181645
0.7857	Intermediate Similarity	NPC166554
0.7857	Intermediate Similarity	NPC265856
0.7843	Intermediate Similarity	NPC300584
0.7835	Intermediate Similarity	NPC472008
0.7778	Intermediate Similarity	NPC99760
0.7778	Intermediate Similarity	NPC114345
0.7778	Intermediate Similarity	NPC6099
0.7778	Intermediate Similarity	NPC303230
0.7745	Intermediate Similarity	NPC20078
0.7745	Intermediate Similarity	NPC473574
0.7732	Intermediate Similarity	NPC23622
0.7732	Intermediate Similarity	NPC472007
0.7714	Intermediate Similarity	NPC473624
0.77	Intermediate Similarity	NPC29798
0.77	Intermediate Similarity	NPC282644
0.7692	Intermediate Similarity	NPC224172
0.7685	Intermediate Similarity	NPC38154
0.7647	Intermediate Similarity	NPC93271
0.7647	Intermediate Similarity	NPC135576
0.7636	Intermediate Similarity	NPC66108
0.7629	Intermediate Similarity	NPC472009
0.757	Intermediate Similarity	NPC478052
0.7568	Intermediate Similarity	NPC478212
0.7553	Intermediate Similarity	NPC162741
0.7553	Intermediate Similarity	NPC91332
0.7549	Intermediate Similarity	NPC91408
0.7526	Intermediate Similarity	NPC187529
0.7526	Intermediate Similarity	NPC307112
0.7523	Intermediate Similarity	NPC471400
0.7523	Intermediate Similarity	NPC101018
0.7522	Intermediate Similarity	NPC478204
0.7522	Intermediate Similarity	NPC53396
0.7522	Intermediate Similarity	NPC98249
0.75	Intermediate Similarity	NPC131864
0.7476	Intermediate Similarity	NPC472733
0.7476	Intermediate Similarity	NPC472734
0.7456	Intermediate Similarity	NPC108581
0.7456	Intermediate Similarity	NPC478206
0.7456	Intermediate Similarity	NPC478205
0.7456	Intermediate Similarity	NPC284707
0.7455	Intermediate Similarity	NPC478209
0.7431	Intermediate Similarity	NPC473807
0.7426	Intermediate Similarity	NPC166110
0.7404	Intermediate Similarity	NPC471694
0.7404	Intermediate Similarity	NPC472731
0.7404	Intermediate Similarity	NPC266842
0.7404	Intermediate Similarity	NPC472732
0.74	Intermediate Similarity	NPC142159
0.74	Intermediate Similarity	NPC307092
0.74	Intermediate Similarity	NPC95364
0.7379	Intermediate Similarity	NPC471698
0.7379	Intermediate Similarity	NPC316215
0.7374	Intermediate Similarity	NPC113370
0.7374	Intermediate Similarity	NPC300779
0.7374	Intermediate Similarity	NPC476079
0.7374	Intermediate Similarity	NPC103743
0.7358	Intermediate Similarity	NPC46998
0.7358	Intermediate Similarity	NPC110443
0.7358	Intermediate Similarity	NPC185141
0.7358	Intermediate Similarity	NPC472637
0.7358	Intermediate Similarity	NPC133907
0.7358	Intermediate Similarity	NPC128733
0.7358	Intermediate Similarity	NPC471401
0.7353	Intermediate Similarity	NPC248193
0.7333	Intermediate Similarity	NPC153776
0.7333	Intermediate Similarity	NPC177680
0.7333	Intermediate Similarity	NPC472730
0.7333	Intermediate Similarity	NPC472729
0.7327	Intermediate Similarity	NPC471399
0.7327	Intermediate Similarity	NPC477684
0.732	Intermediate Similarity	NPC475083
0.73	Intermediate Similarity	NPC87189
0.73	Intermediate Similarity	NPC473658
0.73	Intermediate Similarity	NPC228415
0.7297	Intermediate Similarity	NPC478211
0.7273	Intermediate Similarity	NPC469483
0.7273	Intermediate Similarity	NPC327106
0.7265	Intermediate Similarity	NPC472000
0.7265	Intermediate Similarity	NPC472001
0.7265	Intermediate Similarity	NPC471999
0.7264	Intermediate Similarity	NPC472728
0.7264	Intermediate Similarity	NPC472727
0.7257	Intermediate Similarity	NPC321496
0.7257	Intermediate Similarity	NPC471204
0.7255	Intermediate Similarity	NPC193396
0.7255	Intermediate Similarity	NPC475441
0.7255	Intermediate Similarity	NPC32944
0.7255	Intermediate Similarity	NPC32552
0.725	Intermediate Similarity	NPC476008
0.7248	Intermediate Similarity	NPC472645
0.7248	Intermediate Similarity	NPC471332
0.7248	Intermediate Similarity	NPC34768
0.7248	Intermediate Similarity	NPC471333
0.7241	Intermediate Similarity	NPC476107
0.7238	Intermediate Similarity	NPC134454
0.7238	Intermediate Similarity	NPC17326
0.7232	Intermediate Similarity	NPC100329
0.7232	Intermediate Similarity	NPC247031
0.7232	Intermediate Similarity	NPC132790
0.7232	Intermediate Similarity	NPC97939
0.7228	Intermediate Similarity	NPC51358
0.7228	Intermediate Similarity	NPC295448
0.7222	Intermediate Similarity	NPC25666
0.7222	Intermediate Similarity	NPC297281
0.7222	Intermediate Similarity	NPC473144
0.7222	Intermediate Similarity	NPC475945
0.7222	Intermediate Similarity	NPC475871
0.7222	Intermediate Similarity	NPC271059
0.7217	Intermediate Similarity	NPC469684
0.7217	Intermediate Similarity	NPC474518
0.7212	Intermediate Similarity	NPC279313
0.7207	Intermediate Similarity	NPC20192
0.7207	Intermediate Similarity	NPC478210
0.7207	Intermediate Similarity	NPC475065
0.7196	Intermediate Similarity	NPC472753
0.7196	Intermediate Similarity	NPC469657
0.7196	Intermediate Similarity	NPC244456
0.7193	Intermediate Similarity	NPC80650
0.7193	Intermediate Similarity	NPC247069
0.7188	Intermediate Similarity	NPC47653
0.7184	Intermediate Similarity	NPC469645
0.7184	Intermediate Similarity	NPC162205
0.7184	Intermediate Similarity	NPC469692
0.7184	Intermediate Similarity	NPC273579
0.7184	Intermediate Similarity	NPC475912
0.7184	Intermediate Similarity	NPC295204
0.7184	Intermediate Similarity	NPC288240
0.7182	Intermediate Similarity	NPC187435
0.7182	Intermediate Similarity	NPC266514
0.7182	Intermediate Similarity	NPC329048
0.7182	Intermediate Similarity	NPC67321
0.7182	Intermediate Similarity	NPC330011
0.7179	Intermediate Similarity	NPC476815
0.7179	Intermediate Similarity	NPC31641
0.7179	Intermediate Similarity	NPC478051
0.717	Intermediate Similarity	NPC83895
0.717	Intermediate Similarity	NPC187761
0.7167	Intermediate Similarity	NPC477745
0.7157	Intermediate Similarity	NPC274075
0.7157	Intermediate Similarity	NPC316228
0.7156	Intermediate Similarity	NPC100487
0.7143	Intermediate Similarity	NPC477786
0.7143	Intermediate Similarity	NPC11396
0.7143	Intermediate Similarity	NPC279722
0.7143	Intermediate Similarity	NPC21302
0.7143	Intermediate Similarity	NPC477784
0.7143	Intermediate Similarity	NPC477785
0.7143	Intermediate Similarity	NPC473859
0.713	Intermediate Similarity	NPC70369
0.713	Intermediate Similarity	NPC478216
0.713	Intermediate Similarity	NPC474747
0.713	Intermediate Similarity	NPC39996
0.713	Intermediate Similarity	NPC149371
0.713	Intermediate Similarity	NPC472754
0.7129	Intermediate Similarity	NPC26078
0.7117	Intermediate Similarity	NPC318363
0.7117	Intermediate Similarity	NPC264819
0.7117	Intermediate Similarity	NPC473482
0.7117	Intermediate Similarity	NPC475418
0.7115	Intermediate Similarity	NPC121825
0.7115	Intermediate Similarity	NPC71589
0.7115	Intermediate Similarity	NPC114162
0.7115	Intermediate Similarity	NPC469819
0.7113	Intermediate Similarity	NPC275766
0.7105	Intermediate Similarity	NPC475966
0.7103	Intermediate Similarity	NPC288876
0.7103	Intermediate Similarity	NPC474012
0.7103	Intermediate Similarity	NPC476299
0.71	Intermediate Similarity	NPC112685
0.7094	Intermediate Similarity	NPC245320
0.7091	Intermediate Similarity	NPC478208
0.7091	Intermediate Similarity	NPC469607
0.7091	Intermediate Similarity	NPC32006
0.7091	Intermediate Similarity	NPC477125
0.7091	Intermediate Similarity	NPC85529
0.7091	Intermediate Similarity	NPC81630
0.7087	Intermediate Similarity	NPC30515
0.7087	Intermediate Similarity	NPC184463
0.7087	Intermediate Similarity	NPC472705
0.7087	Intermediate Similarity	NPC476705
0.7087	Intermediate Similarity	NPC472010
0.7083	Intermediate Similarity	NPC24651
0.708	Intermediate Similarity	NPC317107
0.708	Intermediate Similarity	NPC476023
0.7075	Intermediate Similarity	NPC40812

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 NPC35717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1508
0.2-0.3	3696
0.3-0.4	2470
0.4-0.5	941
0.5-0.6	308
0.6-0.7	40
0.7-0.8	3
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
0.6975	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD7983	Approved
0.6923	Remote Similarity	NPD7115	Discovery
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6852	Remote Similarity	NPD4225	Approved
0.6833	Remote Similarity	NPD8517	Approved
0.6833	Remote Similarity	NPD8515	Approved
0.6833	Remote Similarity	NPD8516	Approved
0.6827	Remote Similarity	NPD6698	Approved
0.6827	Remote Similarity	NPD46	Approved
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6101	Approved
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5282	Discontinued
0.6609	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6411	Approved
0.6581	Remote Similarity	NPD6053	Discontinued
0.656	Remote Similarity	NPD8074	Phase 3
0.6552	Remote Similarity	NPD6371	Approved
0.6435	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4756	Discovery
0.6355	Remote Similarity	NPD5785	Approved
0.6355	Remote Similarity	NPD7838	Discovery
0.6344	Remote Similarity	NPD7331	Phase 2
0.6337	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD7154	Phase 3
0.6311	Remote Similarity	NPD6110	Phase 1
0.6306	Remote Similarity	NPD4755	Approved
0.6286	Remote Similarity	NPD5786	Approved
0.6283	Remote Similarity	NPD5344	Discontinued
0.6271	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6686	Approved
0.6228	Remote Similarity	NPD5211	Phase 2
0.6218	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7839	Suspended
0.6214	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD6675	Approved
0.6207	Remote Similarity	NPD7128	Approved
0.6207	Remote Similarity	NPD5739	Approved
0.6207	Remote Similarity	NPD6402	Approved
0.6195	Remote Similarity	NPD5286	Approved
0.6195	Remote Similarity	NPD4700	Approved
0.6195	Remote Similarity	NPD6648	Approved
0.6195	Remote Similarity	NPD4696	Approved
0.6195	Remote Similarity	NPD5285	Approved
0.619	Remote Similarity	NPD1696	Phase 3
0.619	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5363	Approved
0.6186	Remote Similarity	NPD6372	Approved
0.6186	Remote Similarity	NPD6373	Approved
0.617	Remote Similarity	NPD3704	Approved
0.6167	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3618	Phase 1
0.6121	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD5369	Approved
0.6111	Remote Similarity	NPD5328	Approved
0.6102	Remote Similarity	NPD6899	Approved
0.6102	Remote Similarity	NPD6881	Approved
0.6102	Remote Similarity	NPD7320	Approved
0.6094	Remote Similarity	NPD7507	Approved
0.6087	Remote Similarity	NPD5225	Approved
0.6087	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD4633	Approved
0.6087	Remote Similarity	NPD5226	Approved
0.6083	Remote Similarity	NPD6649	Approved
0.6083	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD6059	Approved
0.608	Remote Similarity	NPD6054	Approved
0.6071	Remote Similarity	NPD4697	Phase 3
0.6063	Remote Similarity	NPD7830	Approved
0.6063	Remote Similarity	NPD7829	Approved
0.6058	Remote Similarity	NPD6435	Approved
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6013	Approved
0.6038	Remote Similarity	NPD1694	Approved
0.6034	Remote Similarity	NPD5175	Approved
0.6034	Remote Similarity	NPD5174	Approved
0.6032	Remote Similarity	NPD6016	Approved
0.6032	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD2067	Discontinued
0.5984	Remote Similarity	NPD4632	Approved
0.5984	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5981	Remote Similarity	NPD5279	Phase 3
0.5969	Remote Similarity	NPD8451	Approved
0.5966	Remote Similarity	NPD6011	Approved
0.595	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8130	Phase 1
0.595	Remote Similarity	NPD6869	Approved
0.595	Remote Similarity	NPD6617	Approved
0.595	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD6399	Phase 3
0.5946	Remote Similarity	NPD4202	Approved
0.5938	Remote Similarity	NPD8328	Phase 3
0.5938	Remote Similarity	NPD7642	Approved
0.5932	Remote Similarity	NPD4768	Approved
0.5932	Remote Similarity	NPD4767	Approved
0.5929	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5222	Approved
0.5929	Remote Similarity	NPD5221	Approved
0.5926	Remote Similarity	NPD7524	Approved
0.5923	Remote Similarity	NPD8448	Approved
0.5906	Remote Similarity	NPD7503	Approved
0.5906	Remote Similarity	NPD8444	Approved
0.5905	Remote Similarity	NPD5209	Approved
0.5905	Remote Similarity	NPD3667	Approved
0.5905	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6882	Approved
0.5897	Remote Similarity	NPD4754	Approved
0.5895	Remote Similarity	NPD7341	Phase 2
0.5891	Remote Similarity	NPD7492	Approved
0.5882	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6412	Phase 2
0.5877	Remote Similarity	NPD7902	Approved
0.5877	Remote Similarity	NPD5173	Approved
0.5865	Remote Similarity	NPD4252	Approved
0.5865	Remote Similarity	NPD7260	Phase 2
0.5865	Remote Similarity	NPD5368	Approved
0.5859	Remote Similarity	NPD8080	Discontinued
0.5851	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6616	Approved
0.5842	Remote Similarity	NPD8039	Approved
0.584	Remote Similarity	NPD7500	Approved
0.5833	Remote Similarity	NPD4730	Approved
0.5833	Remote Similarity	NPD4729	Approved
0.5833	Remote Similarity	NPD5128	Approved
0.5833	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7638	Approved
0.582	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD4753	Phase 2
0.5802	Remote Similarity	NPD7078	Approved
0.5802	Remote Similarity	NPD8293	Discontinued
0.5798	Remote Similarity	NPD6008	Approved
0.5794	Remote Similarity	NPD7328	Approved
0.5794	Remote Similarity	NPD3133	Approved
0.5794	Remote Similarity	NPD3665	Phase 1
0.5794	Remote Similarity	NPD4786	Approved
0.5794	Remote Similarity	NPD7641	Discontinued
0.5794	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD3666	Approved
0.5794	Remote Similarity	NPD7327	Approved
0.5789	Remote Similarity	NPD8390	Approved
0.5789	Remote Similarity	NPD8391	Approved
0.5789	Remote Similarity	NPD8392	Approved
0.5781	Remote Similarity	NPD6921	Approved
0.5776	Remote Similarity	NPD7639	Approved
0.5776	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD8340	Approved
0.5769	Remote Similarity	NPD8342	Approved
0.5769	Remote Similarity	NPD8341	Approved
0.5769	Remote Similarity	NPD8299	Approved
0.576	Remote Similarity	NPD6274	Approved
0.5758	Remote Similarity	NPD7736	Approved
0.5752	Remote Similarity	NPD7748	Approved
0.5748	Remote Similarity	NPD7516	Approved
0.5741	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6084	Phase 2
0.5738	Remote Similarity	NPD5251	Approved
0.5738	Remote Similarity	NPD5248	Approved
0.5738	Remote Similarity	NPD5250	Approved
0.5738	Remote Similarity	NPD5247	Approved
0.5738	Remote Similarity	NPD5249	Phase 3
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4695	Discontinued
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD5281	Approved
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5284	Approved
0.5714	Remote Similarity	NPD4821	Approved
0.5714	Remote Similarity	NPD7515	Phase 2
0.5702	Remote Similarity	NPD4629	Approved
0.5702	Remote Similarity	NPD5210	Approved
0.5702	Remote Similarity	NPD5695	Phase 3
0.5701	Remote Similarity	NPD6695	Phase 3
0.5701	Remote Similarity	NPD5362	Discontinued
0.5691	Remote Similarity	NPD5216	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