NPASS Compound

Structure

NPC20578 OpenBabel07101719252D 28 32 0 0 1 0 0 0 0 0999 V2000 -5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 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 0.8660 0.5000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 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 -0.5000 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 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 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 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -0.0000 -0.0000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 28 1 0 0 0 0 14 16 2 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 6 0 0 0 18 22 1 0 0 0 0 18 23 1 1 0 0 0 19 23 1 1 0 0 0 19 24 1 0 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 25 1 1 0 0 0 21 27 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.28
Volume:	419.272
LogP:	4.44
LogD:	4.065
LogS:	-4.49
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	4.853
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.832
MDCK Permeability:	1.7228654542122968e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.236
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.645
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405
Plasma Protein Binding (PPB):	94.73001098632812%
Volume Distribution (VD):	1.464
Pgp-substrate:	5.965271949768066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.381
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.761
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	10.91
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.152
Carcinogencity:	0.528
Eye Corrosion:	0.014
Eye Irritation:	0.45
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC20578

Natural Product ID:	NPC20578
*Common Name:**	Sesterstatin 4
IUPAC Name:	(4R,5aS,5bR,7aS,11aS,11bR,13R,13aS)-5b,8,8,11a,13a-pentamethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydrophenanthro[2,1-e][2]benzofuran-4,13-diol
Synonyms:	Sesterstatin 4
Standard InCHIKey:	YOOYCQNQJUSJJV-MMRGFKSUSA-N
Standard InCHI:	InChI=1S/C25H38O3/c1-22(2)8-6-9-23(3)18(22)7-10-24(4)19(23)12-21(27)25(5)16-14-28-13-15(16)17(26)11-20(24)25/h13-14,17-21,26-27H,6-12H2,1-5H3/t17-,18+,19-,20+,21-,23+,24-,25-/m1/s1
SMILES:	O[C@@H]1C[C@H]2[C@]3(C)CC[C@@H]4[C@]([C@H]3C[C@H]([C@@]2(c2c1coc2)C)O)(C)CCCC4(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL304790
PubChem CID:	10045715
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
ED50	2
GI50	13

Activity Type	# Activity
Cell Line	14
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI50	=	4.9	ug.mL-1	PMID[537304]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	1.6	ug.mL-1	PMID[537304]
NPT6484	Cell Line	KAT-4 cell line		GI50	=	2.0	ug.mL-1	PMID[537304]
NPT763	Cell Line	SW-1736	Homo sapiens	GI50	=	2.1	ug.mL-1	PMID[537304]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	1.8	ug.mL-1	PMID[537304]
NPT1216	Cell Line	FaDu	Homo sapiens	GI50	=	2.0	ug.mL-1	PMID[537304]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	1.6	ug.mL-1	PMID[537304]
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.87	ug ml-1	PMID[537304]
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.9	ug ml-1	PMID[537305]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	1.6	ug.mL-1	PMID[537305]
NPT763	Cell Line	SW-1736	Homo sapiens	GI50	=	2.1	ug.mL-1	PMID[537305]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	1.8	ug.mL-1	PMID[537305]
NPT1216	Cell Line	FaDu	Homo sapiens	GI50	=	2.0	ug.mL-1	PMID[537305]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	1.6	ug.mL-1	PMID[537305]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2.0	ug.mL-1	PMID[537305]

☑ 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 NPC20578 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	335
0.1-0.2	1371
0.2-0.3	3131
0.3-0.4	5562
0.4-0.5	10447
0.5-0.6	11107
0.6-0.7	8940
0.7-0.8	1525
0.8-0.85	223
0.85-0.9	47
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62103
0.9638	High Similarity	NPC41182
0.9627	High Similarity	NPC4764
0.9353	High Similarity	NPC103134
0.9124	High Similarity	NPC214572
0.9078	High Similarity	NPC64568
0.9058	High Similarity	NPC310043
0.8919	High Similarity	NPC35000
0.8912	High Similarity	NPC469503
0.8889	High Similarity	NPC97904
0.8867	High Similarity	NPC474611
0.8857	High Similarity	NPC471996
0.8851	High Similarity	NPC282445
0.8851	High Similarity	NPC30222
0.8851	High Similarity	NPC178932
0.8792	High Similarity	NPC469336
0.875	High Similarity	NPC476944
0.8732	High Similarity	NPC67003
0.8731	High Similarity	NPC303010
0.8707	High Similarity	NPC195325
0.8707	High Similarity	NPC472654
0.8684	High Similarity	NPC335761
0.8681	High Similarity	NPC476946
0.8675	High Similarity	NPC249021
0.8671	High Similarity	NPC205765
0.8627	High Similarity	NPC200782
0.86	High Similarity	NPC114880
0.8582	High Similarity	NPC272899
0.8582	High Similarity	NPC46896
0.8581	High Similarity	NPC211625
0.8571	High Similarity	NPC250228
0.8571	High Similarity	NPC302369
0.8571	High Similarity	NPC134254
0.8571	High Similarity	NPC39986
0.8571	High Similarity	NPC471998
0.8562	High Similarity	NPC5676
0.8561	High Similarity	NPC471995
0.8553	High Similarity	NPC472772
0.8552	High Similarity	NPC243577
0.8543	High Similarity	NPC472785
0.8533	High Similarity	NPC475777
0.8523	High Similarity	NPC196864
0.8523	High Similarity	NPC476122
0.8523	High Similarity	NPC477404
0.8523	High Similarity	NPC469335
0.8523	High Similarity	NPC159927
0.8506	High Similarity	NPC82851
0.8506	High Similarity	NPC69028
0.8506	High Similarity	NPC5079
0.8497	Intermediate Similarity	NPC307383
0.8483	Intermediate Similarity	NPC121158
0.8478	Intermediate Similarity	NPC120836
0.8478	Intermediate Similarity	NPC198904
0.8478	Intermediate Similarity	NPC223063
0.8477	Intermediate Similarity	NPC57998
0.8471	Intermediate Similarity	NPC296558
0.8452	Intermediate Similarity	NPC198047
0.8452	Intermediate Similarity	NPC477405
0.8452	Intermediate Similarity	NPC51568
0.8452	Intermediate Similarity	NPC234660
0.8446	Intermediate Similarity	NPC216755
0.8425	Intermediate Similarity	NPC205071
0.8421	Intermediate Similarity	NPC75310
0.8411	Intermediate Similarity	NPC476201
0.8411	Intermediate Similarity	NPC75906
0.8408	Intermediate Similarity	NPC472282
0.8397	Intermediate Similarity	NPC276551
0.8397	Intermediate Similarity	NPC470182
0.8397	Intermediate Similarity	NPC470940
0.8387	Intermediate Similarity	NPC329938
0.8387	Intermediate Similarity	NPC207978
0.8387	Intermediate Similarity	NPC263432
0.8387	Intermediate Similarity	NPC211777
0.8387	Intermediate Similarity	NPC472771
0.838	Intermediate Similarity	NPC158525
0.8378	Intermediate Similarity	NPC62799
0.8378	Intermediate Similarity	NPC346
0.8377	Intermediate Similarity	NPC475967
0.8369	Intermediate Similarity	NPC214097
0.8367	Intermediate Similarity	NPC251865
0.8366	Intermediate Similarity	NPC107646
0.8357	Intermediate Similarity	NPC61788
0.8356	Intermediate Similarity	NPC263337
0.8354	Intermediate Similarity	NPC271235
0.8344	Intermediate Similarity	NPC97574
0.8344	Intermediate Similarity	NPC472787
0.8344	Intermediate Similarity	NPC93172
0.8344	Intermediate Similarity	NPC470875
0.8333	Intermediate Similarity	NPC469338
0.8333	Intermediate Similarity	NPC224394
0.8333	Intermediate Similarity	NPC88841
0.8333	Intermediate Similarity	NPC663
0.8333	Intermediate Similarity	NPC288602
0.8333	Intermediate Similarity	NPC125182
0.8333	Intermediate Similarity	NPC470998
0.8333	Intermediate Similarity	NPC292389
0.8333	Intermediate Similarity	NPC472773
0.8333	Intermediate Similarity	NPC69647
0.8323	Intermediate Similarity	NPC477402
0.8323	Intermediate Similarity	NPC472653
0.8322	Intermediate Similarity	NPC221809
0.8322	Intermediate Similarity	NPC470941
0.8322	Intermediate Similarity	NPC255414
0.8322	Intermediate Similarity	NPC471174
0.8312	Intermediate Similarity	NPC299038
0.8312	Intermediate Similarity	NPC472778
0.8312	Intermediate Similarity	NPC45101
0.8312	Intermediate Similarity	NPC261597
0.8312	Intermediate Similarity	NPC472777
0.8312	Intermediate Similarity	NPC472776
0.8301	Intermediate Similarity	NPC469850
0.8301	Intermediate Similarity	NPC476262
0.8301	Intermediate Similarity	NPC44675
0.8301	Intermediate Similarity	NPC264943
0.8301	Intermediate Similarity	NPC214541
0.828	Intermediate Similarity	NPC476857
0.828	Intermediate Similarity	NPC476858
0.828	Intermediate Similarity	NPC476856
0.828	Intermediate Similarity	NPC469849
0.8278	Intermediate Similarity	NPC212257
0.8269	Intermediate Similarity	NPC188649
0.8269	Intermediate Similarity	NPC193798
0.8269	Intermediate Similarity	NPC470792
0.8267	Intermediate Similarity	NPC19747
0.8267	Intermediate Similarity	NPC471007
0.8258	Intermediate Similarity	NPC475226
0.8258	Intermediate Similarity	NPC477403
0.8252	Intermediate Similarity	NPC476947
0.8248	Intermediate Similarity	NPC130275
0.8248	Intermediate Similarity	NPC83115
0.8247	Intermediate Similarity	NPC41880
0.8247	Intermediate Similarity	NPC209364
0.8239	Intermediate Similarity	NPC160651
0.8239	Intermediate Similarity	NPC471397
0.8224	Intermediate Similarity	NPC18135
0.8217	Intermediate Similarity	NPC419
0.8207	Intermediate Similarity	NPC476943
0.8205	Intermediate Similarity	NPC475381
0.8205	Intermediate Similarity	NPC25255
0.8194	Intermediate Similarity	NPC36655
0.8194	Intermediate Similarity	NPC286722
0.8194	Intermediate Similarity	NPC472283
0.8194	Intermediate Similarity	NPC304692
0.8194	Intermediate Similarity	NPC194499
0.8188	Intermediate Similarity	NPC230979
0.8188	Intermediate Similarity	NPC185456
0.8187	Intermediate Similarity	NPC82602
0.8182	Intermediate Similarity	NPC92979
0.8176	Intermediate Similarity	NPC173516
0.8176	Intermediate Similarity	NPC223415
0.8176	Intermediate Similarity	NPC476853
0.8176	Intermediate Similarity	NPC476861
0.8176	Intermediate Similarity	NPC472775
0.8176	Intermediate Similarity	NPC100333
0.8176	Intermediate Similarity	NPC472651
0.8176	Intermediate Similarity	NPC472784
0.8176	Intermediate Similarity	NPC476850
0.8176	Intermediate Similarity	NPC472774
0.817	Intermediate Similarity	NPC121615
0.817	Intermediate Similarity	NPC44577
0.817	Intermediate Similarity	NPC476939
0.817	Intermediate Similarity	NPC476940
0.817	Intermediate Similarity	NPC294511
0.817	Intermediate Similarity	NPC472672
0.817	Intermediate Similarity	NPC33938
0.8165	Intermediate Similarity	NPC271657
0.8165	Intermediate Similarity	NPC123088
0.8158	Intermediate Similarity	NPC156189
0.8158	Intermediate Similarity	NPC196846
0.8158	Intermediate Similarity	NPC470997
0.8153	Intermediate Similarity	NPC470939
0.8153	Intermediate Similarity	NPC18347
0.8153	Intermediate Similarity	NPC117986
0.8153	Intermediate Similarity	NPC79571
0.8153	Intermediate Similarity	NPC149896
0.8153	Intermediate Similarity	NPC96443
0.8153	Intermediate Similarity	NPC290400
0.8153	Intermediate Similarity	NPC18986
0.8151	Intermediate Similarity	NPC90953
0.8141	Intermediate Similarity	NPC475295
0.8141	Intermediate Similarity	NPC116639
0.8141	Intermediate Similarity	NPC140952
0.8141	Intermediate Similarity	NPC473473
0.8141	Intermediate Similarity	NPC262872
0.8138	Intermediate Similarity	NPC310830
0.8134	Intermediate Similarity	NPC212918
0.8129	Intermediate Similarity	NPC104736
0.8129	Intermediate Similarity	NPC469485
0.8129	Intermediate Similarity	NPC126723
0.8125	Intermediate Similarity	NPC472652
0.8121	Intermediate Similarity	NPC142113
0.8121	Intermediate Similarity	NPC84479
0.8117	Intermediate Similarity	NPC98206
0.8117	Intermediate Similarity	NPC237259
0.8117	Intermediate Similarity	NPC302054
0.8117	Intermediate Similarity	NPC34421
0.8117	Intermediate Similarity	NPC253201
0.8113	Intermediate Similarity	NPC121995
0.8113	Intermediate Similarity	NPC23387
0.8113	Intermediate Similarity	NPC100849

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 NPC20578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	1005
0.2-0.3	2128
0.3-0.4	2671
0.4-0.5	1945
0.5-0.6	847
0.6-0.7	237
0.7-0.8	14
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD5761	Phase 2
0.8919	High Similarity	NPD5760	Phase 2
0.7647	Intermediate Similarity	NPD8434	Phase 2
0.7531	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2800	Approved
0.7333	Intermediate Similarity	NPD6959	Discontinued
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2533	Approved
0.7325	Intermediate Similarity	NPD2532	Approved
0.7325	Intermediate Similarity	NPD2534	Approved
0.7278	Intermediate Similarity	NPD6273	Approved
0.7179	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7819	Suspended
0.7073	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5494	Approved
0.7052	Intermediate Similarity	NPD6765	Approved
0.7052	Intermediate Similarity	NPD6764	Approved
0.7052	Intermediate Similarity	NPD6559	Discontinued
0.7048	Intermediate Similarity	NPD3749	Approved
0.7032	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4380	Phase 2
0.6988	Remote Similarity	NPD7768	Phase 2
0.6987	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2344	Approved
0.6977	Remote Similarity	NPD5844	Phase 1
0.6951	Remote Similarity	NPD7411	Suspended
0.6948	Remote Similarity	NPD6651	Approved
0.6943	Remote Similarity	NPD1549	Phase 2
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3226	Approved
0.6923	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD920	Approved
0.6909	Remote Similarity	NPD1934	Approved
0.6901	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6166	Phase 2
0.6901	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6785	Approved
0.6893	Remote Similarity	NPD6784	Approved
0.6886	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1471	Phase 3
0.6875	Remote Similarity	NPD8313	Approved
0.6875	Remote Similarity	NPD8312	Approved
0.6867	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7473	Discontinued
0.6855	Remote Similarity	NPD7003	Approved
0.6855	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7075	Discontinued
0.6845	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7458	Discontinued
0.6821	Remote Similarity	NPD3818	Discontinued
0.6813	Remote Similarity	NPD2309	Approved
0.6807	Remote Similarity	NPD37	Approved
0.6802	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6599	Discontinued
0.6786	Remote Similarity	NPD4967	Phase 2
0.6786	Remote Similarity	NPD4965	Approved
0.6786	Remote Similarity	NPD3882	Suspended
0.6786	Remote Similarity	NPD4966	Approved
0.6784	Remote Similarity	NPD6232	Discontinued
0.6784	Remote Similarity	NPD5711	Approved
0.6784	Remote Similarity	NPD5710	Approved
0.6782	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2346	Discontinued
0.677	Remote Similarity	NPD7236	Approved
0.677	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2801	Approved
0.6752	Remote Similarity	NPD1510	Phase 2
0.6752	Remote Similarity	NPD7033	Discontinued
0.6743	Remote Similarity	NPD7074	Phase 3
0.6731	Remote Similarity	NPD1607	Approved
0.671	Remote Similarity	NPD1240	Approved
0.6709	Remote Similarity	NPD1551	Phase 2
0.6707	Remote Similarity	NPD6801	Discontinued
0.6688	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1243	Approved
0.6686	Remote Similarity	NPD7229	Phase 3
0.6686	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6648	Remote Similarity	NPD7472	Approved
0.6646	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD2799	Discontinued
0.6633	Remote Similarity	NPD8404	Phase 2
0.6629	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7228	Approved
0.6628	Remote Similarity	NPD1247	Approved
0.6627	Remote Similarity	NPD5402	Approved
0.6626	Remote Similarity	NPD1511	Approved
0.6611	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6234	Discontinued
0.6604	Remote Similarity	NPD2935	Discontinued
0.6603	Remote Similarity	NPD4140	Approved
0.66	Remote Similarity	NPD1608	Approved
0.659	Remote Similarity	NPD3787	Discontinued
0.6581	Remote Similarity	NPD2313	Discontinued
0.6581	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2797	Approved
0.6573	Remote Similarity	NPD7251	Discontinued
0.6566	Remote Similarity	NPD7239	Suspended
0.6561	Remote Similarity	NPD5735	Approved
0.6545	Remote Similarity	NPD1512	Approved
0.6538	Remote Similarity	NPD8032	Phase 2
0.6536	Remote Similarity	NPD7808	Phase 3
0.6536	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7799	Discontinued
0.6534	Remote Similarity	NPD7177	Discontinued
0.6534	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3751	Discontinued
0.6529	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3817	Phase 2
0.6524	Remote Similarity	NPD7390	Discontinued
0.6524	Remote Similarity	NPD6799	Approved
0.6517	Remote Similarity	NPD6797	Phase 2
0.6512	Remote Similarity	NPD919	Approved
0.651	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5403	Approved
0.6503	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3972	Approved
0.6484	Remote Similarity	NPD8150	Discontinued
0.6474	Remote Similarity	NPD3764	Approved
0.6474	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3268	Approved
0.6471	Remote Similarity	NPD8455	Phase 2
0.6457	Remote Similarity	NPD3926	Phase 2
0.6456	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5124	Phase 1
0.6455	Remote Similarity	NPD6779	Approved
0.6455	Remote Similarity	NPD6778	Approved
0.6455	Remote Similarity	NPD6782	Approved
0.6455	Remote Similarity	NPD6776	Approved
0.6455	Remote Similarity	NPD6781	Approved
0.6455	Remote Similarity	NPD6780	Approved
0.6455	Remote Similarity	NPD6777	Approved
0.6452	Remote Similarity	NPD4908	Phase 1
0.6452	Remote Similarity	NPD6832	Phase 2
0.6447	Remote Similarity	NPD5327	Phase 3
0.6444	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7698	Approved
0.644	Remote Similarity	NPD7435	Discontinued
0.644	Remote Similarity	NPD7697	Approved
0.644	Remote Similarity	NPD7696	Phase 3
0.6438	Remote Similarity	NPD3748	Approved
0.6438	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7199	Phase 2
0.6429	Remote Similarity	NPD2798	Approved
0.6424	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6844	Discontinued
0.6406	Remote Similarity	NPD7870	Phase 2
0.6406	Remote Similarity	NPD7871	Phase 2
0.6405	Remote Similarity	NPD6696	Suspended
0.64	Remote Similarity	NPD17	Approved
0.6398	Remote Similarity	NPD5406	Approved
0.6398	Remote Similarity	NPD5404	Approved
0.6398	Remote Similarity	NPD5405	Approved
0.6398	Remote Similarity	NPD5408	Approved
0.6389	Remote Similarity	NPD7240	Approved
0.6387	Remote Similarity	NPD2861	Phase 2
0.6387	Remote Similarity	NPD3057	Approved
0.6386	Remote Similarity	NPD5401	Approved
0.638	Remote Similarity	NPD6674	Discontinued
0.6375	Remote Similarity	NPD7097	Phase 1
0.6374	Remote Similarity	NPD1465	Phase 2
0.6364	Remote Similarity	NPD4360	Phase 2
0.6364	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4363	Phase 3
0.6353	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6355	Discontinued
0.6341	Remote Similarity	NPD8166	Discontinued
0.6341	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2296	Approved
0.6335	Remote Similarity	NPD4308	Phase 3
0.6329	Remote Similarity	NPD6663	Approved
0.6328	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD4287	Approved
0.6323	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4111	Phase 1
0.6318	Remote Similarity	NPD4665	Approved
0.6316	Remote Similarity	NPD7577	Discontinued
0.6316	Remote Similarity	NPD6280	Approved
0.6316	Remote Similarity	NPD1201	Approved
0.6316	Remote Similarity	NPD6279	Approved
0.6313	Remote Similarity	NPD7286	Phase 2

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