NPASS Compound

Structure

NPC171395 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 2.3087 2.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7848 3.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4337 4.9377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1823 1.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6758 4.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3815 2.8540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 -1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0762 2.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2251 3.6050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1324 4.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 1.2286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0488 5.0627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9273 0.3013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3966 0.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1788 3.8077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1540 6.0164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0662 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1765 1.6795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3662 0.9926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9760 4.7614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 19 2 0 0 0 0 3 19 1 0 0 0 0 5 21 1 0 0 0 0 8 9 2 0 0 0 0 8 22 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 30 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 21 32 2 0 0 0 0 21 36 1 0 0 0 0 22 29 1 0 0 0 0 23 33 2 0 0 0 0 24 9 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 31 1 1 0 0 0 26 29 1 1 0 0 0 27 31 1 1 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 30 36 1 0 0 0 0 31 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.3
Volume:	536.002
LogP:	4.597
LogD:	3.482
LogS:	-4.687
# Rotatable Bonds:	9
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	5.202
Fsp3:	0.645
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:	-5.239
MDCK Permeability:	2.5882334739435464e-05
Pgp-inhibitor:	0.184
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.482
30% Bioavailability (F30%):	0.618

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.9
Plasma Protein Binding (PPB):	89.94648742675781%
Volume Distribution (VD):	0.37
Pgp-substrate:	11.021533966064453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.403
CYP3A4-substrate:	0.834

ADMET: Excretion

Clearance (CL):	0.866
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.245
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.956
Carcinogencity:	0.796
Eye Corrosion:	0.027
Eye Irritation:	0.05
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC171395

Natural Product ID:	NPC171395
*Common Name:**	Norselic Acid E
IUPAC Name:	(8R,9S,10R,13S,14S,17R)-17-[(2R,5R)-5-acetyloxy-5-ethyl-6-methylhept-6-en-2-yl]-10-methyl-3-oxo-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms:	Norselic Acid E
Standard InCHIKey:	JFWKHVJJUMJZAN-RKDCWTDHSA-N
Standard InCHI:	InChI=1S/C31H42O5/c1-7-30(19(2)3,36-21(5)32)16-12-20(4)25-10-11-27-24-9-8-22-18-23(33)13-15-29(22,6)26(24)14-17-31(25,27)28(34)35/h8-9,13,15,18,20,24-27H,2,7,10-12,14,16-17H2,1,3-6H3,(H,34,35)/t20-,24-,25-,26+,27+,29+,30-,31+/m1/s1
SMILES:	CC[C@@](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C(=O)O)(C(=C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221672
PubChem CID:	44557652
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33060	crella sp.	Species	Crellidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[19848433]

☑ 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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.6	uM	PMID[538222]

☑ 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 NPC171395 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	172
0.1-0.2	928
0.2-0.3	3986
0.3-0.4	11076
0.4-0.5	11635
0.5-0.6	7554
0.6-0.7	5478
0.7-0.8	1703
0.8-0.85	147
0.85-0.9	16
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9438	High Similarity	NPC204341
0.9	High Similarity	NPC262043
0.8778	High Similarity	NPC136948
0.8764	High Similarity	NPC29447
0.875	High Similarity	NPC69279
0.875	High Similarity	NPC83569
0.8737	High Similarity	NPC476253
0.866	High Similarity	NPC99411
0.8602	High Similarity	NPC474018
0.8602	High Similarity	NPC473986
0.8542	High Similarity	NPC202705
0.8539	High Similarity	NPC470015
0.8539	High Similarity	NPC310470
0.8539	High Similarity	NPC168188
0.8523	High Similarity	NPC201912
0.8523	High Similarity	NPC477372
0.8523	High Similarity	NPC38350
0.8515	High Similarity	NPC220155
0.8478	Intermediate Similarity	NPC72397
0.8454	Intermediate Similarity	NPC57079
0.8454	Intermediate Similarity	NPC98868
0.8454	Intermediate Similarity	NPC166745
0.8454	Intermediate Similarity	NPC108368
0.8454	Intermediate Similarity	NPC235464
0.8444	Intermediate Similarity	NPC87552
0.8444	Intermediate Similarity	NPC164577
0.8427	Intermediate Similarity	NPC260956
0.8427	Intermediate Similarity	NPC320514
0.8416	Intermediate Similarity	NPC91034
0.8416	Intermediate Similarity	NPC475294
0.84	Intermediate Similarity	NPC472868
0.8387	Intermediate Similarity	NPC285982
0.8387	Intermediate Similarity	NPC173042
0.8387	Intermediate Similarity	NPC5509
0.8384	Intermediate Similarity	NPC475320
0.8352	Intermediate Similarity	NPC94531
0.8352	Intermediate Similarity	NPC311702
0.8352	Intermediate Similarity	NPC123319
0.835	Intermediate Similarity	NPC473627
0.835	Intermediate Similarity	NPC37116
0.8333	Intermediate Similarity	NPC295347
0.8333	Intermediate Similarity	NPC477373
0.8333	Intermediate Similarity	NPC97913
0.8333	Intermediate Similarity	NPC293052
0.8317	Intermediate Similarity	NPC189863
0.8317	Intermediate Similarity	NPC266570
0.8316	Intermediate Similarity	NPC472871
0.8315	Intermediate Similarity	NPC147066
0.8315	Intermediate Similarity	NPC278459
0.83	Intermediate Similarity	NPC470954
0.8298	Intermediate Similarity	NPC472866
0.8298	Intermediate Similarity	NPC476369
0.8298	Intermediate Similarity	NPC476437
0.8295	Intermediate Similarity	NPC477371
0.8295	Intermediate Similarity	NPC196827
0.8295	Intermediate Similarity	NPC274996
0.828	Intermediate Similarity	NPC24816
0.828	Intermediate Similarity	NPC472870
0.828	Intermediate Similarity	NPC117122
0.8269	Intermediate Similarity	NPC474315
0.8261	Intermediate Similarity	NPC472869
0.8247	Intermediate Similarity	NPC155676
0.8247	Intermediate Similarity	NPC472941
0.8247	Intermediate Similarity	NPC456
0.8242	Intermediate Similarity	NPC472865
0.8229	Intermediate Similarity	NPC476415
0.8222	Intermediate Similarity	NPC133391
0.8222	Intermediate Similarity	NPC3511
0.8222	Intermediate Similarity	NPC321289
0.8222	Intermediate Similarity	NPC100297
0.8222	Intermediate Similarity	NPC327969
0.8222	Intermediate Similarity	NPC296367
0.8222	Intermediate Similarity	NPC142253
0.82	Intermediate Similarity	NPC32577
0.82	Intermediate Similarity	NPC155332
0.82	Intermediate Similarity	NPC114540
0.8191	Intermediate Similarity	NPC36668
0.8191	Intermediate Similarity	NPC284561
0.8191	Intermediate Similarity	NPC118011
0.8191	Intermediate Similarity	NPC474570
0.8191	Intermediate Similarity	NPC66344
0.8191	Intermediate Similarity	NPC305039
0.8191	Intermediate Similarity	NPC177141
0.819	Intermediate Similarity	NPC221144
0.819	Intermediate Similarity	NPC191620
0.819	Intermediate Similarity	NPC236217
0.8182	Intermediate Similarity	NPC74410
0.8173	Intermediate Similarity	NPC29133
0.8173	Intermediate Similarity	NPC16270
0.8172	Intermediate Similarity	NPC128644
0.8172	Intermediate Similarity	NPC75315
0.8172	Intermediate Similarity	NPC477228
0.8172	Intermediate Similarity	NPC163016
0.8172	Intermediate Similarity	NPC236618
0.8172	Intermediate Similarity	NPC136548
0.8163	Intermediate Similarity	NPC208094
0.8163	Intermediate Similarity	NPC253826
0.8155	Intermediate Similarity	NPC472825
0.8152	Intermediate Similarity	NPC470048
0.8152	Intermediate Similarity	NPC269638
0.8152	Intermediate Similarity	NPC474537
0.8152	Intermediate Similarity	NPC473038
0.8152	Intermediate Similarity	NPC189311
0.8152	Intermediate Similarity	NPC11711
0.8152	Intermediate Similarity	NPC8571
0.8144	Intermediate Similarity	NPC33473
0.8144	Intermediate Similarity	NPC20546
0.8144	Intermediate Similarity	NPC209355
0.8132	Intermediate Similarity	NPC279639
0.8132	Intermediate Similarity	NPC474976
0.8132	Intermediate Similarity	NPC3856
0.8132	Intermediate Similarity	NPC49019
0.8132	Intermediate Similarity	NPC474790
0.8131	Intermediate Similarity	NPC476963
0.8125	Intermediate Similarity	NPC152897
0.8125	Intermediate Similarity	NPC66429
0.8119	Intermediate Similarity	NPC329345
0.8119	Intermediate Similarity	NPC112009
0.8119	Intermediate Similarity	NPC180204
0.8119	Intermediate Similarity	NPC473283
0.8119	Intermediate Similarity	NPC475526
0.8119	Intermediate Similarity	NPC72151
0.8105	Intermediate Similarity	NPC175628
0.8105	Intermediate Similarity	NPC477149
0.8105	Intermediate Similarity	NPC477147
0.8105	Intermediate Similarity	NPC111585
0.8105	Intermediate Similarity	NPC474842
0.8105	Intermediate Similarity	NPC129913
0.8105	Intermediate Similarity	NPC148414
0.8105	Intermediate Similarity	NPC475965
0.81	Intermediate Similarity	NPC476240
0.81	Intermediate Similarity	NPC168319
0.81	Intermediate Similarity	NPC194028
0.81	Intermediate Similarity	NPC224720
0.81	Intermediate Similarity	NPC310981
0.81	Intermediate Similarity	NPC146822
0.81	Intermediate Similarity	NPC476223
0.8095	Intermediate Similarity	NPC470961
0.8085	Intermediate Similarity	NPC472302
0.8081	Intermediate Similarity	NPC471717
0.8081	Intermediate Similarity	NPC92275
0.8081	Intermediate Similarity	NPC197386
0.8077	Intermediate Similarity	NPC137911
0.8077	Intermediate Similarity	NPC228477
0.8065	Intermediate Similarity	NPC186975
0.8065	Intermediate Similarity	NPC6247
0.8065	Intermediate Similarity	NPC472863
0.8061	Intermediate Similarity	NPC250757
0.8061	Intermediate Similarity	NPC301534
0.8061	Intermediate Similarity	NPC190713
0.8061	Intermediate Similarity	NPC328371
0.8043	Intermediate Similarity	NPC320801
0.8043	Intermediate Similarity	NPC19849
0.8043	Intermediate Similarity	NPC209882
0.8043	Intermediate Similarity	NPC473246
0.8043	Intermediate Similarity	NPC472864
0.8041	Intermediate Similarity	NPC56525
0.8041	Intermediate Similarity	NPC469406
0.8041	Intermediate Similarity	NPC184870
0.8039	Intermediate Similarity	NPC473175
0.8037	Intermediate Similarity	NPC470953
0.8037	Intermediate Similarity	NPC474181
0.8022	Intermediate Similarity	NPC193347
0.8022	Intermediate Similarity	NPC469805
0.8022	Intermediate Similarity	NPC469799
0.8022	Intermediate Similarity	NPC469806
0.8022	Intermediate Similarity	NPC469804
0.8022	Intermediate Similarity	NPC472239
0.8021	Intermediate Similarity	NPC26888
0.8021	Intermediate Similarity	NPC218301
0.8021	Intermediate Similarity	NPC19114
0.8021	Intermediate Similarity	NPC470113
0.802	Intermediate Similarity	NPC473163
0.802	Intermediate Similarity	NPC320447
0.8019	Intermediate Similarity	NPC475524
0.8019	Intermediate Similarity	NPC100267
0.8	Intermediate Similarity	NPC84271
0.8	Intermediate Similarity	NPC287833
0.8	Intermediate Similarity	NPC54705
0.8	Intermediate Similarity	NPC241221
0.8	Intermediate Similarity	NPC35751
0.8	Intermediate Similarity	NPC476274
0.8	Intermediate Similarity	NPC266955
0.8	Intermediate Similarity	NPC102414
0.8	Intermediate Similarity	NPC474889
0.8	Intermediate Similarity	NPC201406
0.8	Intermediate Similarity	NPC214387
0.8	Intermediate Similarity	NPC174342
0.8	Intermediate Similarity	NPC77168
0.8	Intermediate Similarity	NPC474844
0.8	Intermediate Similarity	NPC227865
0.7981	Intermediate Similarity	NPC475418
0.7981	Intermediate Similarity	NPC473482
0.7981	Intermediate Similarity	NPC318363
0.798	Intermediate Similarity	NPC110937
0.798	Intermediate Similarity	NPC108078
0.798	Intermediate Similarity	NPC141401
0.798	Intermediate Similarity	NPC2049
0.798	Intermediate Similarity	NPC57416
0.798	Intermediate Similarity	NPC107243

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 NPC171395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1119
0.2-0.3	3542
0.3-0.4	2842
0.4-0.5	951
0.5-0.6	245
0.6-0.7	151
0.7-0.8	128
0.8-0.85	12
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8804	High Similarity	NPD5284	Approved
0.8804	High Similarity	NPD5281	Approved
0.8602	High Similarity	NPD6050	Approved
0.8602	High Similarity	NPD5694	Approved
0.8495	Intermediate Similarity	NPD5692	Phase 3
0.8495	Intermediate Similarity	NPD5207	Approved
0.8404	Intermediate Similarity	NPD5693	Phase 1
0.8333	Intermediate Similarity	NPD5695	Phase 3
0.8261	Intermediate Similarity	NPD5690	Phase 2
0.8261	Intermediate Similarity	NPD5280	Approved
0.8261	Intermediate Similarity	NPD4694	Approved
0.8191	Intermediate Similarity	NPD6080	Approved
0.8191	Intermediate Similarity	NPD6904	Approved
0.8191	Intermediate Similarity	NPD6673	Approved
0.8163	Intermediate Similarity	NPD6084	Phase 2
0.8163	Intermediate Similarity	NPD6083	Phase 2
0.8085	Intermediate Similarity	NPD6672	Approved
0.8085	Intermediate Similarity	NPD5737	Approved
0.8022	Intermediate Similarity	NPD4221	Approved
0.8022	Intermediate Similarity	NPD4223	Phase 3
0.7959	Intermediate Similarity	NPD5654	Approved
0.7957	Intermediate Similarity	NPD5329	Approved
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.79	Intermediate Similarity	NPD5696	Approved
0.7895	Intermediate Similarity	NPD5208	Approved
0.7872	Intermediate Similarity	NPD6098	Approved
0.7872	Intermediate Similarity	NPD5279	Phase 3
0.7872	Intermediate Similarity	NPD7521	Approved
0.7872	Intermediate Similarity	NPD7334	Approved
0.7872	Intermediate Similarity	NPD6409	Approved
0.7872	Intermediate Similarity	NPD7146	Approved
0.7872	Intermediate Similarity	NPD5330	Approved
0.7872	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD4197	Approved
0.7822	Intermediate Similarity	NPD6404	Discontinued
0.7812	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6881	Approved
0.781	Intermediate Similarity	NPD6899	Approved
0.78	Intermediate Similarity	NPD5959	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD4096	Approved
0.7727	Intermediate Similarity	NPD5733	Approved
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD4687	Approved
0.7714	Intermediate Similarity	NPD5697	Approved
0.7708	Intermediate Similarity	NPD6903	Approved
0.7708	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4518	Approved
0.7692	Intermediate Similarity	NPD4195	Approved
0.7684	Intermediate Similarity	NPD5205	Approved
0.7684	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4688	Approved
0.7684	Intermediate Similarity	NPD4693	Phase 3
0.7684	Intermediate Similarity	NPD4689	Approved
0.7684	Intermediate Similarity	NPD4690	Approved
0.7684	Intermediate Similarity	NPD4138	Approved
0.7664	Intermediate Similarity	NPD7102	Approved
0.7664	Intermediate Similarity	NPD7290	Approved
0.7664	Intermediate Similarity	NPD6883	Approved
0.7653	Intermediate Similarity	NPD6079	Approved
0.7642	Intermediate Similarity	NPD6011	Approved
0.7634	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD4753	Phase 2
0.7619	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD7128	Approved
0.7619	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD5739	Approved
0.7604	Intermediate Similarity	NPD3573	Approved
0.76	Intermediate Similarity	NPD4629	Approved
0.76	Intermediate Similarity	NPD5210	Approved
0.7593	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7593	Intermediate Similarity	NPD6847	Approved
0.7593	Intermediate Similarity	NPD6650	Approved
0.7593	Intermediate Similarity	NPD6617	Approved
0.7593	Intermediate Similarity	NPD6869	Approved
0.7576	Intermediate Similarity	NPD5133	Approved
0.757	Intermediate Similarity	NPD6013	Approved
0.757	Intermediate Similarity	NPD6014	Approved
0.757	Intermediate Similarity	NPD6012	Approved
0.7549	Intermediate Similarity	NPD7638	Approved
0.7528	Intermediate Similarity	NPD4058	Approved
0.7523	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD6001	Approved
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD5276	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7476	Intermediate Similarity	NPD7640	Approved
0.7476	Intermediate Similarity	NPD7639	Approved
0.7474	Intermediate Similarity	NPD3666	Approved
0.7474	Intermediate Similarity	NPD4786	Approved
0.7474	Intermediate Similarity	NPD3665	Phase 1
0.7474	Intermediate Similarity	NPD3133	Approved
0.7449	Intermediate Similarity	NPD5328	Approved
0.7419	Intermediate Similarity	NPD4695	Discontinued
0.7407	Intermediate Similarity	NPD6372	Approved
0.7407	Intermediate Similarity	NPD6373	Approved
0.7396	Intermediate Similarity	NPD1694	Approved
0.7391	Intermediate Similarity	NPD3617	Approved
0.7383	Intermediate Similarity	NPD5701	Approved
0.7383	Intermediate Similarity	NPD6614	Approved
0.7353	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5222	Approved
0.7353	Intermediate Similarity	NPD5221	Approved
0.734	Intermediate Similarity	NPD4139	Approved
0.734	Intermediate Similarity	NPD4692	Approved
0.7333	Intermediate Similarity	NPD5211	Phase 2
0.732	Intermediate Similarity	NPD3618	Phase 1
0.7308	Intermediate Similarity	NPD4696	Approved
0.7308	Intermediate Similarity	NPD5285	Approved
0.7308	Intermediate Similarity	NPD5286	Approved
0.73	Intermediate Similarity	NPD7515	Phase 2
0.73	Intermediate Similarity	NPD6411	Approved
0.7282	Intermediate Similarity	NPD5173	Approved
0.7282	Intermediate Similarity	NPD7902	Approved
0.7273	Intermediate Similarity	NPD6051	Approved
0.7273	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6052	Approved
0.7263	Intermediate Similarity	NPD3667	Approved
0.7238	Intermediate Similarity	NPD5223	Approved
0.7228	Intermediate Similarity	NPD4202	Approved
0.72	Intermediate Similarity	NPD5785	Approved
0.7196	Intermediate Similarity	NPD5141	Approved
0.7193	Intermediate Similarity	NPD6335	Approved
0.7191	Intermediate Similarity	NPD4747	Approved
0.7191	Intermediate Similarity	NPD4691	Approved
0.7188	Intermediate Similarity	NPD4788	Approved
0.7184	Intermediate Similarity	NPD7614	Phase 1
0.717	Intermediate Similarity	NPD5225	Approved
0.717	Intermediate Similarity	NPD4633	Approved
0.717	Intermediate Similarity	NPD5226	Approved
0.717	Intermediate Similarity	NPD5091	Approved
0.717	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.713	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD7100	Approved
0.7115	Intermediate Similarity	NPD4755	Approved
0.7105	Intermediate Similarity	NPD6317	Approved
0.7103	Intermediate Similarity	NPD5174	Approved
0.7103	Intermediate Similarity	NPD5175	Approved
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4137	Phase 3
0.7065	Intermediate Similarity	NPD8039	Approved
0.7054	Intermediate Similarity	NPD6053	Discontinued
0.7043	Intermediate Similarity	NPD6313	Approved
0.7043	Intermediate Similarity	NPD6314	Approved
0.7021	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4697	Phase 3
0.7018	Intermediate Similarity	NPD6274	Approved
0.701	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6686	Approved
0.699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7900	Approved
0.6981	Remote Similarity	NPD4700	Approved
0.6972	Remote Similarity	NPD6008	Approved
0.6961	Remote Similarity	NPD8034	Phase 2
0.6961	Remote Similarity	NPD7637	Suspended
0.6961	Remote Similarity	NPD8035	Phase 2
0.6957	Remote Similarity	NPD4785	Approved
0.6957	Remote Similarity	NPD4784	Approved
0.6957	Remote Similarity	NPD6009	Approved
0.6939	Remote Similarity	NPD3668	Phase 3
0.6923	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD4243	Approved
0.6911	Remote Similarity	NPD7260	Phase 2
0.6909	Remote Similarity	NPD6412	Phase 2
0.6893	Remote Similarity	NPD5779	Approved
0.6893	Remote Similarity	NPD5778	Approved
0.6891	Remote Similarity	NPD7604	Phase 2
0.6869	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7503	Approved
0.6864	Remote Similarity	NPD5983	Phase 2
0.6864	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7732	Phase 3
0.6852	Remote Similarity	NPD7632	Discontinued
0.6847	Remote Similarity	NPD4730	Approved
0.6847	Remote Similarity	NPD4729	Approved
0.6833	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD4754	Approved
0.678	Remote Similarity	NPD6054	Approved
0.6777	Remote Similarity	NPD6616	Approved
0.6777	Remote Similarity	NPD6336	Discontinued
0.6762	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6081	Approved
0.6735	Remote Similarity	NPD5209	Approved
0.6729	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD5249	Phase 3
0.6726	Remote Similarity	NPD5251	Approved
0.6726	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5247	Approved
0.6726	Remote Similarity	NPD5135	Approved
0.6726	Remote Similarity	NPD5250	Approved
0.6726	Remote Similarity	NPD5169	Approved
0.6726	Remote Similarity	NPD5248	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