NPASS Compound

Structure

NPC132753 OpenBabel07101718282D 32 36 0 0 1 0 0 0 0 0999 V2000 9.7350 -0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7350 -0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2350 0.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 8.2350 -1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 31 1 0 0 0 0 15 24 1 0 0 0 0 15 32 1 0 0 0 0 16 28 2 0 0 0 0 16 32 1 0 0 0 0 17 22 2 0 0 0 0 18 24 1 1 0 0 0 18 25 1 0 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 24 2 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	468.808
LogP:	4.35
LogD:	4.032
LogS:	-4.381
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	4.935
Fsp3:	0.815
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:	-5.146
MDCK Permeability:	2.805310214171186e-05
Pgp-inhibitor:	0.872
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.367
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	95.16056060791016%
Volume Distribution (VD):	1.274
Pgp-substrate:	2.752720594406128%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.499
CYP2C9-inhibitor:	0.305
CYP2C9-substrate:	0.448
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	3.761
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.71
Carcinogencity:	0.046
Eye Corrosion:	0.005
Eye Irritation:	0.329
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC132753

Natural Product ID:	NPC132753
*Common Name:**	3-Acetyl Sesterstatin 1
IUPAC Name:	[(5aS,5bR,7aR,8R,11aR,11bR,13R,13aS)-13-hydroxy-5b,8,11a,13a-tetramethyl-1-oxo-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[2,1-e][2]benzofuran-8-yl]methyl acetate
Synonyms:	3-Acetyl Sesterstatin 1
Standard InCHIKey:	HBZMFBSNLZLYMN-HHZCAVKLSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-16(28)32-15-24(2)10-6-11-25(3)18(24)9-12-26(4)19-8-7-17-14-31-23(30)22(17)27(19,5)21(29)13-20(25)26/h18-21,29H,6-15H2,1-5H3/t18-,19-,20+,21+,24-,25-,26-,27+/m0/s1
SMILES:	CC(=O)OC[C@]1(C)CCC[C@]2([C@H]1CC[C@@]1([C@@H]2C[C@H]([C@]2([C@H]1CCC1=C2C(=O)OC1)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457152
PubChem CID:	21629516
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11809054]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[16124771]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16378375]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584401]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Maldives	n.a.	PMID[9873492]

☑ 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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>=	1.0	ug.mL-1	PMID[496904]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>=	1.0	ug.mL-1	PMID[496904]
NPT81	Cell Line	A549	Homo sapiens	IC50	>=	1.0	ug.mL-1	PMID[496904]

☑ 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 NPC132753 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	228
0.1-0.2	1395
0.2-0.3	4356
0.3-0.4	9725
0.4-0.5	11938
0.5-0.6	6485
0.6-0.7	5435
0.7-0.8	2849
0.8-0.85	248
0.85-0.9	19
0.9-0.95	8
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC121402
1.0	High Similarity	NPC151681
1.0	High Similarity	NPC224356
1.0	High Similarity	NPC175351
0.9889	High Similarity	NPC472362
0.9889	High Similarity	NPC472363
0.9889	High Similarity	NPC154526
0.9574	High Similarity	NPC165250
0.9474	High Similarity	NPC471208
0.9091	High Similarity	NPC325054
0.89	High Similarity	NPC275539
0.89	High Similarity	NPC189075
0.89	High Similarity	NPC300614
0.89	High Similarity	NPC90946
0.8812	High Similarity	NPC31522
0.88	High Similarity	NPC110496
0.8776	High Similarity	NPC476081
0.8681	High Similarity	NPC250981
0.8673	High Similarity	NPC471075
0.866	High Similarity	NPC478056
0.8632	High Similarity	NPC91010
0.8571	High Similarity	NPC201406
0.8571	High Similarity	NPC476299
0.8571	High Similarity	NPC474012
0.8571	High Similarity	NPC117685
0.8558	High Similarity	NPC194951
0.8558	High Similarity	NPC12046
0.8542	High Similarity	NPC183012
0.8526	High Similarity	NPC139692
0.8515	High Similarity	NPC478052
0.85	High Similarity	NPC112009
0.85	High Similarity	NPC254202
0.85	High Similarity	NPC120321
0.85	High Similarity	NPC159533
0.8485	Intermediate Similarity	NPC235142
0.8485	Intermediate Similarity	NPC63249
0.8485	Intermediate Similarity	NPC303559
0.8476	Intermediate Similarity	NPC157441
0.8469	Intermediate Similarity	NPC234617
0.8469	Intermediate Similarity	NPC124703
0.8454	Intermediate Similarity	NPC327179
0.8438	Intermediate Similarity	NPC471720
0.8431	Intermediate Similarity	NPC301666
0.8431	Intermediate Similarity	NPC187435
0.8431	Intermediate Similarity	NPC67321
0.8421	Intermediate Similarity	NPC233345
0.8421	Intermediate Similarity	NPC187722
0.8421	Intermediate Similarity	NPC235704
0.8421	Intermediate Similarity	NPC186363
0.84	Intermediate Similarity	NPC134077
0.84	Intermediate Similarity	NPC273005
0.84	Intermediate Similarity	NPC295791
0.84	Intermediate Similarity	NPC469606
0.84	Intermediate Similarity	NPC31058
0.84	Intermediate Similarity	NPC476890
0.84	Intermediate Similarity	NPC136289
0.8381	Intermediate Similarity	NPC476163
0.8367	Intermediate Similarity	NPC253826
0.8367	Intermediate Similarity	NPC38530
0.8367	Intermediate Similarity	NPC84335
0.8333	Intermediate Similarity	NPC474436
0.8333	Intermediate Similarity	NPC472303
0.8333	Intermediate Similarity	NPC214756
0.8333	Intermediate Similarity	NPC272075
0.8333	Intermediate Similarity	NPC158059
0.8333	Intermediate Similarity	NPC34768
0.8333	Intermediate Similarity	NPC295643
0.8333	Intermediate Similarity	NPC49776
0.8333	Intermediate Similarity	NPC63118
0.8333	Intermediate Similarity	NPC202728
0.8333	Intermediate Similarity	NPC469607
0.8333	Intermediate Similarity	NPC229281
0.8333	Intermediate Similarity	NPC118519
0.8317	Intermediate Similarity	NPC180204
0.8317	Intermediate Similarity	NPC478057
0.8317	Intermediate Similarity	NPC476889
0.8317	Intermediate Similarity	NPC95899
0.8317	Intermediate Similarity	NPC324001
0.8316	Intermediate Similarity	NPC227467
0.8316	Intermediate Similarity	NPC78973
0.8316	Intermediate Similarity	NPC210037
0.8316	Intermediate Similarity	NPC280149
0.8316	Intermediate Similarity	NPC477872
0.8316	Intermediate Similarity	NPC221111
0.8316	Intermediate Similarity	NPC474728
0.8316	Intermediate Similarity	NPC273621
0.8316	Intermediate Similarity	NPC18872
0.8316	Intermediate Similarity	NPC7260
0.8316	Intermediate Similarity	NPC120968
0.8316	Intermediate Similarity	NPC290614
0.8302	Intermediate Similarity	NPC25909
0.83	Intermediate Similarity	NPC476888
0.83	Intermediate Similarity	NPC81530
0.83	Intermediate Similarity	NPC93744
0.83	Intermediate Similarity	NPC471412
0.8298	Intermediate Similarity	NPC277771
0.8283	Intermediate Similarity	NPC471966
0.8283	Intermediate Similarity	NPC164349
0.8283	Intermediate Similarity	NPC194196
0.828	Intermediate Similarity	NPC185638
0.828	Intermediate Similarity	NPC56588
0.8265	Intermediate Similarity	NPC134072
0.8265	Intermediate Similarity	NPC116457
0.8265	Intermediate Similarity	NPC235053
0.8265	Intermediate Similarity	NPC242848
0.8265	Intermediate Similarity	NPC234993
0.8265	Intermediate Similarity	NPC7124
0.8261	Intermediate Similarity	NPC171789
0.8247	Intermediate Similarity	NPC74751
0.8247	Intermediate Similarity	NPC6818
0.8247	Intermediate Similarity	NPC191412
0.8247	Intermediate Similarity	NPC474554
0.8247	Intermediate Similarity	NPC114159
0.8235	Intermediate Similarity	NPC222161
0.8229	Intermediate Similarity	NPC329842
0.8229	Intermediate Similarity	NPC158030
0.8229	Intermediate Similarity	NPC105189
0.8229	Intermediate Similarity	NPC4036
0.8229	Intermediate Similarity	NPC470590
0.8229	Intermediate Similarity	NPC65120
0.8229	Intermediate Similarity	NPC77099
0.8229	Intermediate Similarity	NPC72845
0.8229	Intermediate Similarity	NPC60755
0.8229	Intermediate Similarity	NPC145067
0.8229	Intermediate Similarity	NPC285184
0.8229	Intermediate Similarity	NPC233455
0.8229	Intermediate Similarity	NPC38754
0.8229	Intermediate Similarity	NPC289479
0.8218	Intermediate Similarity	NPC32577
0.8218	Intermediate Similarity	NPC80781
0.8218	Intermediate Similarity	NPC162973
0.8218	Intermediate Similarity	NPC40918
0.8218	Intermediate Similarity	NPC155332
0.8218	Intermediate Similarity	NPC273668
0.8218	Intermediate Similarity	NPC137430
0.8218	Intermediate Similarity	NPC114540
0.8211	Intermediate Similarity	NPC290972
0.8211	Intermediate Similarity	NPC198664
0.8211	Intermediate Similarity	NPC5509
0.8211	Intermediate Similarity	NPC174342
0.8211	Intermediate Similarity	NPC64872
0.8211	Intermediate Similarity	NPC470588
0.8211	Intermediate Similarity	NPC274330
0.8211	Intermediate Similarity	NPC25906
0.8211	Intermediate Similarity	NPC30522
0.8211	Intermediate Similarity	NPC143232
0.8208	Intermediate Similarity	NPC277769
0.82	Intermediate Similarity	NPC474190
0.82	Intermediate Similarity	NPC307954
0.82	Intermediate Similarity	NPC251680
0.82	Intermediate Similarity	NPC47024
0.82	Intermediate Similarity	NPC471413
0.82	Intermediate Similarity	NPC476767
0.8191	Intermediate Similarity	NPC312561
0.8191	Intermediate Similarity	NPC305029
0.8182	Intermediate Similarity	NPC89225
0.8182	Intermediate Similarity	NPC51499
0.8182	Intermediate Similarity	NPC259788
0.8182	Intermediate Similarity	NPC170131
0.8182	Intermediate Similarity	NPC474343
0.8182	Intermediate Similarity	NPC255589
0.8173	Intermediate Similarity	NPC306265
0.8172	Intermediate Similarity	NPC474013
0.8172	Intermediate Similarity	NPC197823
0.8163	Intermediate Similarity	NPC96916
0.8163	Intermediate Similarity	NPC290481
0.8163	Intermediate Similarity	NPC276110
0.8163	Intermediate Similarity	NPC139570
0.8163	Intermediate Similarity	NPC53565
0.8155	Intermediate Similarity	NPC478208
0.8144	Intermediate Similarity	NPC86368
0.8144	Intermediate Similarity	NPC271652
0.8144	Intermediate Similarity	NPC169343
0.8144	Intermediate Similarity	NPC477436
0.8144	Intermediate Similarity	NPC53555
0.8144	Intermediate Similarity	NPC477435
0.8137	Intermediate Similarity	NPC8196
0.8137	Intermediate Similarity	NPC99266
0.8137	Intermediate Similarity	NPC36688
0.8137	Intermediate Similarity	NPC476237
0.8137	Intermediate Similarity	NPC90177
0.8131	Intermediate Similarity	NPC122056
0.8125	Intermediate Similarity	NPC470589
0.8125	Intermediate Similarity	NPC8062
0.8125	Intermediate Similarity	NPC130278
0.8125	Intermediate Similarity	NPC111110
0.8125	Intermediate Similarity	NPC198818
0.8125	Intermediate Similarity	NPC161638
0.8125	Intermediate Similarity	NPC126369
0.8125	Intermediate Similarity	NPC193750
0.8125	Intermediate Similarity	NPC120840
0.8125	Intermediate Similarity	NPC472307
0.8125	Intermediate Similarity	NPC113989
0.8125	Intermediate Similarity	NPC281942
0.8125	Intermediate Similarity	NPC291028
0.8125	Intermediate Similarity	NPC232426
0.8119	Intermediate Similarity	NPC54909
0.8119	Intermediate Similarity	NPC473160
0.8119	Intermediate Similarity	NPC472637
0.8119	Intermediate Similarity	NPC233012

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 NPC132753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1692
0.2-0.3	3625
0.3-0.4	2362
0.4-0.5	798
0.5-0.6	231
0.6-0.7	175
0.7-0.8	66
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD7902	Approved
0.8283	Intermediate Similarity	NPD7638	Approved
0.8247	Intermediate Similarity	NPD7748	Approved
0.8229	Intermediate Similarity	NPD7515	Phase 2
0.82	Intermediate Similarity	NPD7639	Approved
0.82	Intermediate Similarity	NPD7640	Approved
0.8095	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7900	Approved
0.8061	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7632	Discontinued
0.8019	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6399	Phase 3
0.7909	Intermediate Similarity	NPD7115	Discovery
0.7857	Intermediate Similarity	NPD8034	Phase 2
0.7857	Intermediate Similarity	NPD8035	Phase 2
0.7745	Intermediate Similarity	NPD4225	Approved
0.7736	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3618	Phase 1
0.766	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5739	Approved
0.7642	Intermediate Similarity	NPD6675	Approved
0.7642	Intermediate Similarity	NPD6402	Approved
0.7642	Intermediate Similarity	NPD7128	Approved
0.7604	Intermediate Similarity	NPD1694	Approved
0.7604	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6372	Approved
0.7593	Intermediate Similarity	NPD6373	Approved
0.7551	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.7475	Intermediate Similarity	NPD5328	Approved
0.7455	Intermediate Similarity	NPD6650	Approved
0.7455	Intermediate Similarity	NPD6649	Approved
0.7407	Intermediate Similarity	NPD5701	Approved
0.7407	Intermediate Similarity	NPD5697	Approved
0.7373	Intermediate Similarity	NPD7507	Approved
0.7364	Intermediate Similarity	NPD6883	Approved
0.7364	Intermediate Similarity	NPD7102	Approved
0.7364	Intermediate Similarity	NPD7290	Approved
0.7347	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD7521	Approved
0.7347	Intermediate Similarity	NPD7334	Approved
0.7347	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD6684	Approved
0.7339	Intermediate Similarity	NPD6011	Approved
0.7327	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD4786	Approved
0.7312	Intermediate Similarity	NPD6116	Phase 1
0.7308	Intermediate Similarity	NPD6084	Phase 2
0.7308	Intermediate Similarity	NPD6083	Phase 2
0.73	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8130	Phase 1
0.7297	Intermediate Similarity	NPD6847	Approved
0.7297	Intermediate Similarity	NPD6869	Approved
0.7297	Intermediate Similarity	NPD6617	Approved
0.7292	Intermediate Similarity	NPD3667	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4202	Approved
0.7232	Intermediate Similarity	NPD6882	Approved
0.7232	Intermediate Similarity	NPD8297	Approved
0.7212	Intermediate Similarity	NPD4697	Phase 3
0.7204	Intermediate Similarity	NPD6117	Approved
0.72	Intermediate Similarity	NPD6903	Approved
0.72	Intermediate Similarity	NPD6672	Approved
0.72	Intermediate Similarity	NPD5737	Approved
0.719	Intermediate Similarity	NPD7319	Approved
0.7156	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3666	Approved
0.713	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3573	Approved
0.7075	Intermediate Similarity	NPD5696	Approved
0.7069	Intermediate Similarity	NPD7328	Approved
0.7069	Intermediate Similarity	NPD7327	Approved
0.7053	Intermediate Similarity	NPD6697	Approved
0.7053	Intermediate Similarity	NPD6115	Approved
0.7053	Intermediate Similarity	NPD6114	Approved
0.7053	Intermediate Similarity	NPD6118	Approved
0.7048	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD5221	Approved
0.7037	Intermediate Similarity	NPD5211	Phase 2
0.7034	Intermediate Similarity	NPD8033	Approved
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4700	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.7009	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5693	Phase 1
0.699	Remote Similarity	NPD6411	Approved
0.6989	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5173	Approved
0.6979	Remote Similarity	NPD7645	Phase 2
0.6952	Remote Similarity	NPD5695	Phase 3
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6944	Remote Similarity	NPD5223	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD6335	Approved
0.6917	Remote Similarity	NPD8328	Phase 3
0.6909	Remote Similarity	NPD5141	Approved
0.6907	Remote Similarity	NPD7525	Registered
0.6897	Remote Similarity	NPD6274	Approved
0.6897	Remote Similarity	NPD6868	Approved
0.6893	Remote Similarity	NPD5785	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6881	Remote Similarity	NPD5225	Approved
0.6881	Remote Similarity	NPD5226	Approved
0.6881	Remote Similarity	NPD5224	Approved
0.6881	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD3617	Approved
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8133	Approved
0.687	Remote Similarity	NPD4632	Approved
0.6864	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD7101	Approved
0.6838	Remote Similarity	NPD6317	Approved
0.6827	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD5284	Approved
0.6818	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD5174	Approved
0.6818	Remote Similarity	NPD4754	Approved
0.68	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3668	Phase 3
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD6051	Approved
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6904	Approved
0.6796	Remote Similarity	NPD6101	Approved
0.6796	Remote Similarity	NPD4753	Phase 2
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6313	Approved
0.678	Remote Similarity	NPD6314	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.675	Remote Similarity	NPD6909	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6908	Approved
0.6735	Remote Similarity	NPD4695	Discontinued
0.6731	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD7614	Phase 1
0.6698	Remote Similarity	NPD6001	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6696	Remote Similarity	NPD4767	Approved
0.6695	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD4519	Discontinued
0.6639	Remote Similarity	NPD7604	Phase 2
0.6636	Remote Similarity	NPD4629	Approved
0.6636	Remote Similarity	NPD5210	Approved
0.6612	Remote Similarity	NPD5983	Phase 2
0.6612	Remote Similarity	NPD7503	Approved
0.66	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD4223	Phase 3
0.6596	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD5128	Approved
0.6579	Remote Similarity	NPD4730	Approved
0.6579	Remote Similarity	NPD4729	Approved
0.6574	Remote Similarity	NPD7732	Phase 3
0.6569	Remote Similarity	NPD5329	Approved
0.6562	Remote Similarity	NPD7339	Approved
0.6562	Remote Similarity	NPD6942	Approved
0.6559	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD4788	Approved
0.6532	Remote Similarity	NPD6336	Discontinued
0.6532	Remote Similarity	NPD6616	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.6529	Remote Similarity	NPD6054	Approved
0.6509	Remote Similarity	NPD6050	Approved
0.6509	Remote Similarity	NPD7637	Suspended
0.6505	Remote Similarity	NPD6098	Approved
0.6495	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5344	Discontinued
0.648	Remote Similarity	NPD7078	Approved
0.648	Remote Similarity	NPD8293	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