NPASS Compound

Structure

CID152117 OpenBabel06191715522D 38 42 0 0 1 0 0 0 0 0999 V2000 -1.6949 2.9357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4204 -0.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4205 -1.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4811 -0.5656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3496 0.4031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5727 -0.5067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0307 -1.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5413 1.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 1.9562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 -1.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -2.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5202 -0.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6949 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0640 0.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6949 1.9571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3887 0.0011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5419 0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3595 -1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8475 0.4893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6950 -0.9786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5419 -2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8475 0.4893 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2747 -1.1249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5421 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5765 -0.1951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8475 -1.4679 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 -2.5424 1.4678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2722 -2.4424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4098 -2.9468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9814 -1.8003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0377 0.6206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8475 1.4679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 22 2 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 25 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 37 1 0 0 0 0 18 33 2 0 0 0 0 18 38 1 0 0 0 0 19 15 1 1 0 0 0 19 20 1 0 0 0 0 20 30 1 1 0 0 0 21 27 1 0 0 0 0 21 34 1 6 0 0 0 22 30 1 0 0 0 0 22 32 1 0 0 0 0 23 31 1 6 0 0 0 23 32 1 0 0 0 0 24 28 1 0 0 0 0 24 31 1 6 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 26 32 1 1 0 0 0 26 38 1 0 0 0 0 27 29 1 0 0 0 0 27 36 1 1 0 0 0 29 37 1 0 0 0 0 30 6 1 1 0 0 0 31 7 1 6 0 0 0 32 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.35
Volume:	561.441
LogP:	3.974
LogD:	3.392
LogS:	-4.487
# Rotatable Bonds:	3
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	5.374
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.98
MDCK Permeability:	3.457962520769797e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.223
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	87.08307647705078%
Volume Distribution (VD):	1.649
Pgp-substrate:	6.70164155960083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.651
CYP3A4-substrate:	0.66

ADMET: Excretion

Clearance (CL):	2.399
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.934
Carcinogencity:	0.058
Eye Corrosion:	0.005
Eye Irritation:	0.018
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC152117

Natural Product ID:	NPC152117
*Common Name:**	Dihydrosapelin E Acetate
IUPAC Name:	[(5R,7R,8R,9R,10R,13S,17S)-17-[(3S,5R,6S)-5,6-dihydroxy-7,7-dimethyloxepan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Standard InCHIKey:	DSJDMQKGNFHTBJ-KGFLTEPUSA-N
Standard InCHI:	InChI=1S/C32H48O6/c1-18(33)38-26-16-24-28(2,3)25(35)12-14-31(24,7)23-11-13-30(6)20(9-10-22(30)32(23,26)8)19-15-21(34)27(36)29(4,5)37-17-19/h10,12,14,19-21,23-24,26-27,34,36H,9,11,13,15-17H2,1-8H3/t19-,20+,21-,23-,24+,26-,27+,30+,31-,32+/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC[C@H]([C@]1(C)CC3)[C@H]1COC([C@H]([C@@H](C1)O)O)(C)C)(C)C=CC(=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386302
PubChem CID:	73348891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO6696	Chukrasia tabularis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6696	Chukrasia tabularis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10033	Turraea pubescens	Species	Meliaceae	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
IC50	2
Others	3

Activity Type	# Activity
Cell Line	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[508978]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[508978]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	0.0	%	PMID[508978]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	6.7	%	PMID[508978]
NPT176	Organism	Artemia salina	Artemia salina	mortality	=	69.8	%	PMID[508978]

☑ 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 NPC152117 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	237
0.1-0.2	1377
0.2-0.3	4408
0.3-0.4	7768
0.4-0.5	12927
0.5-0.6	7051
0.6-0.7	6037
0.7-0.8	2771
0.8-0.85	108
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234042
0.9429	High Similarity	NPC5284
0.9346	High Similarity	NPC255017
0.9333	High Similarity	NPC41405
0.8929	High Similarity	NPC161065
0.8857	High Similarity	NPC264048
0.885	High Similarity	NPC241192
0.8727	High Similarity	NPC474516
0.8716	High Similarity	NPC197428
0.8716	High Similarity	NPC250956
0.8661	High Similarity	NPC302471
0.8654	High Similarity	NPC470066
0.8654	High Similarity	NPC470067
0.8585	High Similarity	NPC473163
0.8571	High Similarity	NPC167974
0.8559	High Similarity	NPC470063
0.8545	High Similarity	NPC239097
0.8532	High Similarity	NPC472219
0.8532	High Similarity	NPC472217
0.8532	High Similarity	NPC472218
0.8519	High Similarity	NPC102352
0.8519	High Similarity	NPC96377
0.8496	Intermediate Similarity	NPC176840
0.8496	Intermediate Similarity	NPC243981
0.8491	Intermediate Similarity	NPC469327
0.8482	Intermediate Similarity	NPC194100
0.8476	Intermediate Similarity	NPC114274
0.8468	Intermediate Similarity	NPC474229
0.8462	Intermediate Similarity	NPC469789
0.8455	Intermediate Similarity	NPC218853
0.8455	Intermediate Similarity	NPC173905
0.8455	Intermediate Similarity	NPC5475
0.8455	Intermediate Similarity	NPC284828
0.8455	Intermediate Similarity	NPC472216
0.844	Intermediate Similarity	NPC473173
0.844	Intermediate Similarity	NPC3316
0.844	Intermediate Similarity	NPC469318
0.844	Intermediate Similarity	NPC144854
0.844	Intermediate Similarity	NPC59530
0.8435	Intermediate Similarity	NPC77689
0.8435	Intermediate Similarity	NPC473636
0.8426	Intermediate Similarity	NPC471293
0.8426	Intermediate Similarity	NPC65523
0.8426	Intermediate Similarity	NPC255309
0.8421	Intermediate Similarity	NPC284068
0.8411	Intermediate Similarity	NPC22388
0.8393	Intermediate Similarity	NPC71348
0.8393	Intermediate Similarity	NPC280782
0.8393	Intermediate Similarity	NPC90769
0.8393	Intermediate Similarity	NPC472002
0.8393	Intermediate Similarity	NPC269530
0.8381	Intermediate Similarity	NPC108078
0.8378	Intermediate Similarity	NPC474567
0.8378	Intermediate Similarity	NPC470065
0.8365	Intermediate Similarity	NPC473415
0.8365	Intermediate Similarity	NPC473170
0.8365	Intermediate Similarity	NPC180557
0.8365	Intermediate Similarity	NPC469329
0.8365	Intermediate Similarity	NPC37787
0.8365	Intermediate Similarity	NPC30677
0.8364	Intermediate Similarity	NPC293850
0.8364	Intermediate Similarity	NPC277017
0.8364	Intermediate Similarity	NPC469844
0.8364	Intermediate Similarity	NPC154608
0.8364	Intermediate Similarity	NPC192813
0.8364	Intermediate Similarity	NPC258323
0.8362	Intermediate Similarity	NPC476961
0.8362	Intermediate Similarity	NPC79579
0.835	Intermediate Similarity	NPC79117
0.8349	Intermediate Similarity	NPC231530
0.8349	Intermediate Similarity	NPC470587
0.8349	Intermediate Similarity	NPC472655
0.8349	Intermediate Similarity	NPC278628
0.8348	Intermediate Similarity	NPC153440
0.8348	Intermediate Similarity	NPC146280
0.8348	Intermediate Similarity	NPC124676
0.8333	Intermediate Similarity	NPC251236
0.8333	Intermediate Similarity	NPC235539
0.8333	Intermediate Similarity	NPC40632
0.8333	Intermediate Similarity	NPC190286
0.8333	Intermediate Similarity	NPC134869
0.8333	Intermediate Similarity	NPC96312
0.8333	Intermediate Similarity	NPC328374
0.8333	Intermediate Similarity	NPC152199
0.8333	Intermediate Similarity	NPC239716
0.8333	Intermediate Similarity	NPC270958
0.8319	Intermediate Similarity	NPC962
0.8319	Intermediate Similarity	NPC250109
0.8319	Intermediate Similarity	NPC293112
0.8319	Intermediate Similarity	NPC473635
0.8319	Intermediate Similarity	NPC25909
0.8319	Intermediate Similarity	NPC49451
0.8319	Intermediate Similarity	NPC471627
0.8319	Intermediate Similarity	NPC471173
0.8305	Intermediate Similarity	NPC473979
0.8305	Intermediate Similarity	NPC11895
0.8304	Intermediate Similarity	NPC201992
0.8302	Intermediate Similarity	NPC470068
0.8291	Intermediate Similarity	NPC67569
0.8291	Intermediate Similarity	NPC46570
0.8291	Intermediate Similarity	NPC202051
0.8288	Intermediate Similarity	NPC310546
0.8286	Intermediate Similarity	NPC91439
0.8276	Intermediate Similarity	NPC211093
0.8276	Intermediate Similarity	NPC469380
0.8276	Intermediate Similarity	NPC473839
0.8276	Intermediate Similarity	NPC475041
0.8276	Intermediate Similarity	NPC473203
0.8276	Intermediate Similarity	NPC5292
0.8273	Intermediate Similarity	NPC471783
0.8273	Intermediate Similarity	NPC9457
0.8273	Intermediate Similarity	NPC44063
0.8269	Intermediate Similarity	NPC240617
0.8261	Intermediate Similarity	NPC471854
0.8261	Intermediate Similarity	NPC134430
0.8246	Intermediate Similarity	NPC472400
0.8246	Intermediate Similarity	NPC18547
0.8246	Intermediate Similarity	NPC473798
0.8246	Intermediate Similarity	NPC474906
0.8246	Intermediate Similarity	NPC243354
0.8241	Intermediate Similarity	NPC473928
0.8235	Intermediate Similarity	NPC473255
0.8235	Intermediate Similarity	NPC8369
0.823	Intermediate Similarity	NPC11252
0.823	Intermediate Similarity	NPC277769
0.823	Intermediate Similarity	NPC289312
0.822	Intermediate Similarity	NPC470265
0.822	Intermediate Similarity	NPC107493
0.822	Intermediate Similarity	NPC170538
0.822	Intermediate Similarity	NPC23786
0.8214	Intermediate Similarity	NPC101450
0.8214	Intermediate Similarity	NPC6206
0.8208	Intermediate Similarity	NPC292133
0.8205	Intermediate Similarity	NPC474585
0.8198	Intermediate Similarity	NPC94529
0.8198	Intermediate Similarity	NPC19412
0.8198	Intermediate Similarity	NPC94942
0.819	Intermediate Similarity	NPC257457
0.819	Intermediate Similarity	NPC297179
0.819	Intermediate Similarity	NPC118638
0.819	Intermediate Similarity	NPC311554
0.8182	Intermediate Similarity	NPC181357
0.8182	Intermediate Similarity	NPC323834
0.8174	Intermediate Similarity	NPC266728
0.8174	Intermediate Similarity	NPC270929
0.8174	Intermediate Similarity	NPC207217
0.8174	Intermediate Similarity	NPC49492
0.8174	Intermediate Similarity	NPC298278
0.8158	Intermediate Similarity	NPC194273
0.8158	Intermediate Similarity	NPC317210
0.8158	Intermediate Similarity	NPC7921
0.8158	Intermediate Similarity	NPC198539
0.8158	Intermediate Similarity	NPC52634
0.8158	Intermediate Similarity	NPC202889
0.8158	Intermediate Similarity	NPC472757
0.8158	Intermediate Similarity	NPC208998
0.8158	Intermediate Similarity	NPC51978
0.8148	Intermediate Similarity	NPC470054
0.8142	Intermediate Similarity	NPC171888
0.8142	Intermediate Similarity	NPC471243
0.8142	Intermediate Similarity	NPC146945
0.8142	Intermediate Similarity	NPC231589
0.8142	Intermediate Similarity	NPC214797
0.8142	Intermediate Similarity	NPC118860
0.8142	Intermediate Similarity	NPC470076
0.8136	Intermediate Similarity	NPC204731
0.8131	Intermediate Similarity	NPC119036
0.8131	Intermediate Similarity	NPC477854
0.813	Intermediate Similarity	NPC471855
0.8125	Intermediate Similarity	NPC258543
0.8125	Intermediate Similarity	NPC246205
0.8125	Intermediate Similarity	NPC170221
0.8125	Intermediate Similarity	NPC10064
0.8125	Intermediate Similarity	NPC27814
0.8125	Intermediate Similarity	NPC118225
0.8125	Intermediate Similarity	NPC2766
0.8125	Intermediate Similarity	NPC241927
0.812	Intermediate Similarity	NPC476960
0.812	Intermediate Similarity	NPC61520
0.812	Intermediate Similarity	NPC469488
0.812	Intermediate Similarity	NPC475775
0.812	Intermediate Similarity	NPC270850
0.812	Intermediate Similarity	NPC470777
0.812	Intermediate Similarity	NPC305260
0.812	Intermediate Similarity	NPC476529
0.8115	Intermediate Similarity	NPC231529
0.8113	Intermediate Similarity	NPC471777
0.8113	Intermediate Similarity	NPC471822
0.8108	Intermediate Similarity	NPC230541
0.8108	Intermediate Similarity	NPC475294
0.8108	Intermediate Similarity	NPC473165
0.8103	Intermediate Similarity	NPC473968
0.8103	Intermediate Similarity	NPC183580
0.8103	Intermediate Similarity	NPC474654
0.8103	Intermediate Similarity	NPC470854
0.8103	Intermediate Similarity	NPC470959
0.8103	Intermediate Similarity	NPC470493
0.8103	Intermediate Similarity	NPC476965
0.8103	Intermediate Similarity	NPC312824
0.8103	Intermediate Similarity	NPC475809

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 NPC152117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1692
0.2-0.3	3787
0.3-0.4	2211
0.4-0.5	754
0.5-0.6	250
0.6-0.7	152
0.7-0.8	95
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD8297	Approved
0.8482	Intermediate Similarity	NPD4632	Approved
0.8364	Intermediate Similarity	NPD6899	Approved
0.8364	Intermediate Similarity	NPD6881	Approved
0.8362	Intermediate Similarity	NPD6319	Approved
0.8304	Intermediate Similarity	NPD8130	Phase 1
0.8273	Intermediate Similarity	NPD5697	Approved
0.8214	Intermediate Similarity	NPD7290	Approved
0.8214	Intermediate Similarity	NPD6883	Approved
0.8214	Intermediate Similarity	NPD7102	Approved
0.8182	Intermediate Similarity	NPD5739	Approved
0.8182	Intermediate Similarity	NPD7128	Approved
0.8182	Intermediate Similarity	NPD6675	Approved
0.8182	Intermediate Similarity	NPD6402	Approved
0.8142	Intermediate Similarity	NPD6617	Approved
0.8142	Intermediate Similarity	NPD6847	Approved
0.8142	Intermediate Similarity	NPD6869	Approved
0.8142	Intermediate Similarity	NPD6649	Approved
0.8142	Intermediate Similarity	NPD6650	Approved
0.8125	Intermediate Similarity	NPD6013	Approved
0.8125	Intermediate Similarity	NPD6012	Approved
0.8125	Intermediate Similarity	NPD6014	Approved
0.8103	Intermediate Similarity	NPD6009	Approved
0.8083	Intermediate Similarity	NPD7492	Approved
0.807	Intermediate Similarity	NPD6882	Approved
0.8051	Intermediate Similarity	NPD6054	Approved
0.8036	Intermediate Similarity	NPD7320	Approved
0.8036	Intermediate Similarity	NPD6011	Approved
0.8033	Intermediate Similarity	NPD7736	Approved
0.8017	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD7604	Phase 2
0.7983	Intermediate Similarity	NPD5983	Phase 2
0.7965	Intermediate Similarity	NPD6373	Approved
0.7965	Intermediate Similarity	NPD6372	Approved
0.7951	Intermediate Similarity	NPD7078	Approved
0.7949	Intermediate Similarity	NPD7115	Discovery
0.7946	Intermediate Similarity	NPD5701	Approved
0.7917	Intermediate Similarity	NPD6370	Approved
0.7905	Intermediate Similarity	NPD6079	Approved
0.7895	Intermediate Similarity	NPD4634	Approved
0.789	Intermediate Similarity	NPD4696	Approved
0.789	Intermediate Similarity	NPD5285	Approved
0.789	Intermediate Similarity	NPD5286	Approved
0.7869	Intermediate Similarity	NPD6336	Discontinued
0.7857	Intermediate Similarity	NPD6008	Approved
0.7833	Intermediate Similarity	NPD6015	Approved
0.7833	Intermediate Similarity	NPD6016	Approved
0.7805	Intermediate Similarity	NPD8293	Discontinued
0.7769	Intermediate Similarity	NPD5988	Approved
0.775	Intermediate Similarity	NPD6059	Approved
0.7748	Intermediate Similarity	NPD5224	Approved
0.7748	Intermediate Similarity	NPD5225	Approved
0.7748	Intermediate Similarity	NPD4633	Approved
0.7748	Intermediate Similarity	NPD5211	Phase 2
0.7748	Intermediate Similarity	NPD5226	Approved
0.7714	Intermediate Similarity	NPD5328	Approved
0.7706	Intermediate Similarity	NPD4755	Approved
0.7679	Intermediate Similarity	NPD5174	Approved
0.7679	Intermediate Similarity	NPD5175	Approved
0.7672	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7100	Approved
0.7667	Intermediate Similarity	NPD7101	Approved
0.7664	Intermediate Similarity	NPD6399	Phase 3
0.7658	Intermediate Similarity	NPD5223	Approved
0.7652	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6412	Phase 2
0.7615	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5222	Approved
0.7615	Intermediate Similarity	NPD5221	Approved
0.7611	Intermediate Similarity	NPD5141	Approved
0.7593	Intermediate Similarity	NPD7748	Approved
0.7583	Intermediate Similarity	NPD6335	Approved
0.7581	Intermediate Similarity	NPD7507	Approved
0.7568	Intermediate Similarity	NPD4700	Approved
0.7565	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6274	Approved
0.7561	Intermediate Similarity	NPD8328	Phase 3
0.7545	Intermediate Similarity	NPD7902	Approved
0.7545	Intermediate Similarity	NPD6083	Phase 2
0.7545	Intermediate Similarity	NPD5173	Approved
0.7545	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6317	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD6053	Discontinued
0.7438	Intermediate Similarity	NPD6314	Approved
0.7438	Intermediate Similarity	NPD6313	Approved
0.7417	Intermediate Similarity	NPD6868	Approved
0.7414	Intermediate Similarity	NPD4730	Approved
0.7414	Intermediate Similarity	NPD6686	Approved
0.7414	Intermediate Similarity	NPD4729	Approved
0.7411	Intermediate Similarity	NPD7640	Approved
0.7411	Intermediate Similarity	NPD7639	Approved
0.7407	Intermediate Similarity	NPD7515	Phase 2
0.7402	Intermediate Similarity	NPD7319	Approved
0.7358	Intermediate Similarity	NPD3573	Approved
0.7355	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4202	Approved
0.7297	Intermediate Similarity	NPD4697	Phase 3
0.7288	Intermediate Similarity	NPD5248	Approved
0.7288	Intermediate Similarity	NPD5249	Phase 3
0.7288	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5247	Approved
0.7288	Intermediate Similarity	NPD5250	Approved
0.7288	Intermediate Similarity	NPD5251	Approved
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5128	Approved
0.7264	Intermediate Similarity	NPD3618	Phase 1
0.7258	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6908	Approved
0.7258	Intermediate Similarity	NPD6909	Approved
0.7241	Intermediate Similarity	NPD4768	Approved
0.7241	Intermediate Similarity	NPD4767	Approved
0.7238	Intermediate Similarity	NPD4786	Approved
0.7227	Intermediate Similarity	NPD5217	Approved
0.7227	Intermediate Similarity	NPD5216	Approved
0.7227	Intermediate Similarity	NPD5215	Approved
0.7217	Intermediate Similarity	NPD4754	Approved
0.7207	Intermediate Similarity	NPD5695	Phase 3
0.7188	Intermediate Similarity	NPD6033	Approved
0.7168	Intermediate Similarity	NPD4225	Approved
0.7168	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.713	Intermediate Similarity	NPD6672	Approved
0.713	Intermediate Similarity	NPD5737	Approved
0.712	Intermediate Similarity	NPD7503	Approved
0.712	Intermediate Similarity	NPD8033	Approved
0.7103	Intermediate Similarity	NPD7146	Approved
0.7103	Intermediate Similarity	NPD6409	Approved
0.7103	Intermediate Similarity	NPD6684	Approved
0.7103	Intermediate Similarity	NPD5330	Approved
0.7103	Intermediate Similarity	NPD7334	Approved
0.7103	Intermediate Similarity	NPD7521	Approved
0.7091	Intermediate Similarity	NPD6411	Approved
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD5127	Approved
0.7064	Intermediate Similarity	NPD4753	Phase 2
0.7054	Intermediate Similarity	NPD5210	Approved
0.7054	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4629	Approved
0.7048	Intermediate Similarity	NPD3667	Approved
0.704	Intermediate Similarity	NPD8294	Approved
0.704	Intermediate Similarity	NPD8377	Approved
0.7034	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7328	Approved
0.7016	Intermediate Similarity	NPD7327	Approved
0.6984	Remote Similarity	NPD8335	Approved
0.6984	Remote Similarity	NPD8378	Approved
0.6984	Remote Similarity	NPD8296	Approved
0.6984	Remote Similarity	NPD8380	Approved
0.6984	Remote Similarity	NPD8379	Approved
0.6983	Remote Similarity	NPD7632	Discontinued
0.6975	Remote Similarity	NPD5168	Approved
0.6972	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6903	Approved
0.6967	Remote Similarity	NPD8133	Approved
0.696	Remote Similarity	NPD7516	Approved
0.6944	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5281	Approved
0.6937	Remote Similarity	NPD5284	Approved
0.6916	Remote Similarity	NPD3665	Phase 1
0.6916	Remote Similarity	NPD3133	Approved
0.6916	Remote Similarity	NPD3666	Approved
0.6911	Remote Similarity	NPD5167	Approved
0.6909	Remote Similarity	NPD6673	Approved
0.6909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6080	Approved
0.6909	Remote Similarity	NPD6904	Approved
0.6909	Remote Similarity	NPD6101	Approved
0.6903	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5344	Discontinued
0.6891	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6067	Discontinued
0.6875	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD5778	Approved
0.6852	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8517	Approved
0.685	Remote Similarity	NPD8516	Approved
0.685	Remote Similarity	NPD6921	Approved
0.685	Remote Similarity	NPD8515	Approved
0.685	Remote Similarity	NPD8513	Phase 3
0.6786	Remote Similarity	NPD7983	Approved
0.6767	Remote Similarity	NPD7260	Phase 2
0.6729	Remote Similarity	NPD4221	Approved
0.6729	Remote Similarity	NPD4223	Phase 3
0.6715	Remote Similarity	NPD6334	Approved
0.6715	Remote Similarity	NPD6333	Approved
0.6698	Remote Similarity	NPD7525	Registered
0.6697	Remote Similarity	NPD1694	Approved
0.6697	Remote Similarity	NPD5329	Approved
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD6698	Approved
0.6693	Remote Similarity	NPD4522	Approved
0.6692	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD6115	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