NPASS Compound

Structure

CID29133 OpenBabel06191715352D 33 37 0 0 1 0 0 0 0 0999 V2000 -5.9072 -0.6681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -2.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5937 -3.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6940 0.9786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6940 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2367 -0.4893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2368 -1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -1.9567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6488 -1.8012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2156 -2.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6051 -1.5980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2593 -2.3245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3904 -1.9567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8470 -0.4893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3467 -2.7311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9572 -3.2543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -1.4674 0.0000 C 0 0 2 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 -3.3904 -2.9344 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5177 -1.1914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 -1.4893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6114 -3.9809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6639 -3.5886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0009 -3.4576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 17 1 0 0 0 0 7 23 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 29 1 0 0 0 0 16 19 2 0 0 0 0 17 27 1 0 0 0 0 18 9 1 6 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 1 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 28 1 6 0 0 0 24 33 1 0 0 0 0 25 31 2 0 0 0 0 25 33 1 0 0 0 0 26 2 1 1 0 0 0 27 3 1 1 0 0 0 28 4 1 6 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	478.194
LogP:	3.402
LogD:	2.321
LogS:	-4.794
# Rotatable Bonds:	3
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	5.302
Fsp3:	0.643
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:	-4.692
MDCK Permeability:	2.8990485589019954e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.239
Human Intestinal Absorption (HIA):	0.558
20% Bioavailability (F20%):	0.651
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.964
Plasma Protein Binding (PPB):	90.61235046386719%
Volume Distribution (VD):	1.265
Pgp-substrate:	4.37642240524292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.172
CYP2C19-substrate:	0.675
CYP2C9-inhibitor:	0.27
CYP2C9-substrate:	0.153
CYP2D6-inhibitor:	0.186
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.729

ADMET: Excretion

Clearance (CL):	5.649
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.85
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.95
Carcinogencity:	0.751
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC29133

Natural Product ID:	NPC29133
*Common Name:**	(2R)-2-[(1R)-1-[(8R,9S,10R,13R,17S)-10,13-Dimethyl-1-Oxo-4,7,8,9,11,12,16,17-Octahydrocyclopenta[A]Phenanthren-17-Yl]-1-Hydroxyethyl]-5-(Hydroxymethyl)-4-Methyl-2,3-Dihydropyran-6-One
IUPAC Name:	(2R)-2-[(1R)-1-[(8R,9S,10R,13R,17S)-10,13-dimethyl-1-oxo-4,7,8,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	ZKTNOURYQAESEW-ZOKBQHMGSA-N
Standard InCHI:	InChI=1S/C28H36O5/c1-16-14-24(33-25(31)19(16)15-29)28(4,32)22-11-10-20-18-9-8-17-6-5-7-23(30)27(17,3)21(18)12-13-26(20,22)2/h5,7-8,10,18,21-22,24,29,32H,6,9,11-15H2,1-4H3/t18-,21-,22-,24+,26-,27-,28+/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@](C)([C@H]1CC=C2[C@@H]3CC=C4CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333676
PubChem CID:	12115994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[18952419]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23316950]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13927	Withania coagulans	Species	Solanaceae	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	4

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38200.0	nM	PMID[480992]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	48.3	%	PMID[480992]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	100.0	%	PMID[480992]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	76.3	%	PMID[480992]
NPT2	Others	Unspecified		IC50	=	12400.0	nM	PMID[480992]
NPT2	Others	Unspecified		Inhibition	=	88.6	%	PMID[480992]

☑ 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 NPC29133 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	207
0.1-0.2	1102
0.2-0.3	3661
0.3-0.4	7297
0.4-0.5	13740
0.5-0.6	7590
0.6-0.7	6767
0.7-0.8	2215
0.8-0.85	87
0.85-0.9	26
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC470961
0.9615	High Similarity	NPC191620
0.932	High Similarity	NPC91034
0.9259	High Similarity	NPC312824
0.9259	High Similarity	NPC470493
0.9259	High Similarity	NPC183580
0.9238	High Similarity	NPC37116
0.9174	High Similarity	NPC186525
0.9167	High Similarity	NPC64318
0.9083	High Similarity	NPC140055
0.9083	High Similarity	NPC167606
0.9083	High Similarity	NPC286528
0.9083	High Similarity	NPC20302
0.9074	High Similarity	NPC147912
0.9074	High Similarity	NPC67259
0.9065	High Similarity	NPC236217
0.9048	High Similarity	NPC220155
0.9	High Similarity	NPC50774
0.9	High Similarity	NPC709
0.8929	High Similarity	NPC46570
0.8919	High Similarity	NPC264954
0.8909	High Similarity	NPC470492
0.8879	High Similarity	NPC473627
0.885	High Similarity	NPC107493
0.8839	High Similarity	NPC474370
0.8818	High Similarity	NPC176840
0.8807	High Similarity	NPC122056
0.8796	High Similarity	NPC474315
0.8761	High Similarity	NPC67569
0.8727	High Similarity	NPC474181
0.8684	High Similarity	NPC470265
0.8684	High Similarity	NPC23786
0.8684	High Similarity	NPC153700
0.8684	High Similarity	NPC88326
0.8624	High Similarity	NPC324683
0.8609	High Similarity	NPC469789
0.8584	High Similarity	NPC473274
0.8534	High Similarity	NPC470494
0.8534	High Similarity	NPC3381
0.8534	High Similarity	NPC8374
0.8534	High Similarity	NPC8369
0.8509	High Similarity	NPC79579
0.8496	Intermediate Similarity	NPC153440
0.8496	Intermediate Similarity	NPC475913
0.8482	Intermediate Similarity	NPC270929
0.8482	Intermediate Similarity	NPC190286
0.8462	Intermediate Similarity	NPC293112
0.8448	Intermediate Similarity	NPC11895
0.844	Intermediate Similarity	NPC475065
0.8435	Intermediate Similarity	NPC473256
0.8435	Intermediate Similarity	NPC470878
0.8431	Intermediate Similarity	NPC53685
0.8426	Intermediate Similarity	NPC329048
0.8426	Intermediate Similarity	NPC330011
0.8421	Intermediate Similarity	NPC474179
0.8421	Intermediate Similarity	NPC473270
0.8421	Intermediate Similarity	NPC5292
0.8421	Intermediate Similarity	NPC475834
0.8416	Intermediate Similarity	NPC303697
0.8411	Intermediate Similarity	NPC473175
0.8407	Intermediate Similarity	NPC470959
0.8407	Intermediate Similarity	NPC243065
0.8407	Intermediate Similarity	NPC476965
0.8381	Intermediate Similarity	NPC474012
0.8381	Intermediate Similarity	NPC476299
0.8378	Intermediate Similarity	NPC69291
0.8376	Intermediate Similarity	NPC81736
0.8376	Intermediate Similarity	NPC172154
0.8362	Intermediate Similarity	NPC170538
0.8349	Intermediate Similarity	NPC473482
0.8349	Intermediate Similarity	NPC318363
0.8349	Intermediate Similarity	NPC475418
0.8348	Intermediate Similarity	NPC474585
0.8333	Intermediate Similarity	NPC115021
0.8333	Intermediate Similarity	NPC329736
0.8318	Intermediate Similarity	NPC470954
0.8302	Intermediate Similarity	NPC473174
0.8302	Intermediate Similarity	NPC469657
0.8302	Intermediate Similarity	NPC244456
0.8286	Intermediate Similarity	NPC98868
0.8286	Intermediate Similarity	NPC316598
0.8273	Intermediate Similarity	NPC41405
0.8261	Intermediate Similarity	NPC270850
0.8261	Intermediate Similarity	NPC61520
0.8261	Intermediate Similarity	NPC305260
0.8257	Intermediate Similarity	NPC473284
0.8257	Intermediate Similarity	NPC475294
0.825	Intermediate Similarity	NPC473593
0.8241	Intermediate Similarity	NPC146731
0.8241	Intermediate Similarity	NPC296950
0.8235	Intermediate Similarity	NPC156797
0.8235	Intermediate Similarity	NPC287903
0.823	Intermediate Similarity	NPC284915
0.823	Intermediate Similarity	NPC470953
0.8224	Intermediate Similarity	NPC473163
0.8224	Intermediate Similarity	NPC475320
0.8214	Intermediate Similarity	NPC470063
0.8214	Intermediate Similarity	NPC221144
0.8205	Intermediate Similarity	NPC269642
0.819	Intermediate Similarity	NPC476253
0.819	Intermediate Similarity	NPC476961
0.819	Intermediate Similarity	NPC53844
0.8182	Intermediate Similarity	NPC472825
0.8173	Intermediate Similarity	NPC171395
0.8167	Intermediate Similarity	NPC245094
0.8155	Intermediate Similarity	NPC474736
0.8151	Intermediate Similarity	NPC473635
0.8148	Intermediate Similarity	NPC475050
0.8148	Intermediate Similarity	NPC476889
0.8136	Intermediate Similarity	NPC473979
0.8131	Intermediate Similarity	NPC472924
0.8131	Intermediate Similarity	NPC310981
0.8131	Intermediate Similarity	NPC99411
0.8115	Intermediate Similarity	NPC231240
0.8113	Intermediate Similarity	NPC478056
0.8113	Intermediate Similarity	NPC197386
0.8113	Intermediate Similarity	NPC166745
0.8113	Intermediate Similarity	NPC471717
0.8113	Intermediate Similarity	NPC235464
0.8108	Intermediate Similarity	NPC173905
0.8108	Intermediate Similarity	NPC5475
0.8108	Intermediate Similarity	NPC137911
0.8108	Intermediate Similarity	NPC284828
0.8108	Intermediate Similarity	NPC228477
0.8108	Intermediate Similarity	NPC472216
0.8103	Intermediate Similarity	NPC475041
0.8099	Intermediate Similarity	NPC476966
0.8095	Intermediate Similarity	NPC472941
0.8095	Intermediate Similarity	NPC456
0.8095	Intermediate Similarity	NPC328371
0.8095	Intermediate Similarity	NPC117133
0.8087	Intermediate Similarity	NPC239273
0.8087	Intermediate Similarity	NPC284068
0.8073	Intermediate Similarity	NPC472868
0.8067	Intermediate Similarity	NPC318135
0.8058	Intermediate Similarity	NPC177037
0.8058	Intermediate Similarity	NPC472814
0.8056	Intermediate Similarity	NPC476890
0.8056	Intermediate Similarity	NPC40918
0.8053	Intermediate Similarity	NPC475524
0.8053	Intermediate Similarity	NPC269530
0.8053	Intermediate Similarity	NPC100267
0.8049	Intermediate Similarity	NPC316915
0.8039	Intermediate Similarity	NPC5509
0.8037	Intermediate Similarity	NPC54705
0.8036	Intermediate Similarity	NPC5103
0.8036	Intermediate Similarity	NPC5284
0.8036	Intermediate Similarity	NPC235014
0.8034	Intermediate Similarity	NPC476962
0.8019	Intermediate Similarity	NPC202705
0.8019	Intermediate Similarity	NPC253826
0.8019	Intermediate Similarity	NPC156546
0.8018	Intermediate Similarity	NPC151393
0.8017	Intermediate Similarity	NPC257457
0.8017	Intermediate Similarity	NPC311554
0.8	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC470075
0.8	Intermediate Similarity	NPC266570
0.8	Intermediate Similarity	NPC33473
0.8	Intermediate Similarity	NPC189863
0.8	Intermediate Similarity	NPC174948
0.8	Intermediate Similarity	NPC476963
0.8	Intermediate Similarity	NPC477125
0.8	Intermediate Similarity	NPC209355
0.8	Intermediate Similarity	NPC173875
0.8	Intermediate Similarity	NPC318282
0.8	Intermediate Similarity	NPC472935
0.8	Intermediate Similarity	NPC469995
0.7983	Intermediate Similarity	NPC120724
0.7982	Intermediate Similarity	NPC95899
0.7982	Intermediate Similarity	NPC475526
0.7982	Intermediate Similarity	NPC469454
0.7982	Intermediate Similarity	NPC324001
0.7982	Intermediate Similarity	NPC264048
0.7982	Intermediate Similarity	NPC72151
0.7982	Intermediate Similarity	NPC329345
0.7982	Intermediate Similarity	NPC255017
0.7982	Intermediate Similarity	NPC25909
0.7982	Intermediate Similarity	NPC112009
0.7982	Intermediate Similarity	NPC239716
0.7982	Intermediate Similarity	NPC469463
0.7982	Intermediate Similarity	NPC469496
0.7982	Intermediate Similarity	NPC473283
0.7981	Intermediate Similarity	NPC472871
0.7966	Intermediate Similarity	NPC129434
0.7965	Intermediate Similarity	NPC317107
0.7963	Intermediate Similarity	NPC224720
0.7963	Intermediate Similarity	NPC476240
0.7963	Intermediate Similarity	NPC93744
0.7963	Intermediate Similarity	NPC476888
0.7963	Intermediate Similarity	NPC476223
0.7963	Intermediate Similarity	NPC282524
0.7961	Intermediate Similarity	NPC477147
0.7961	Intermediate Similarity	NPC477149
0.7961	Intermediate Similarity	NPC472307
0.7961	Intermediate Similarity	NPC273199
0.7961	Intermediate Similarity	NPC15059
0.7961	Intermediate Similarity	NPC51486
0.7951	Intermediate Similarity	NPC231529
0.7949	Intermediate Similarity	NPC473636

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 NPC29133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1384
0.2-0.3	3385
0.3-0.4	2644
0.4-0.5	1007
0.5-0.6	289
0.6-0.7	237
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9083	High Similarity	NPD7115	Discovery
0.7944	Intermediate Similarity	NPD4225	Approved
0.7719	Intermediate Similarity	NPD6371	Approved
0.7685	Intermediate Similarity	NPD6084	Phase 2
0.7685	Intermediate Similarity	NPD6083	Phase 2
0.7664	Intermediate Similarity	NPD5695	Phase 3
0.7619	Intermediate Similarity	NPD5785	Approved
0.7586	Intermediate Similarity	NPD8297	Approved
0.7544	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD6899	Approved
0.7544	Intermediate Similarity	NPD6881	Approved
0.7477	Intermediate Similarity	NPD6399	Phase 3
0.7456	Intermediate Similarity	NPD5697	Approved
0.7438	Intermediate Similarity	NPD6319	Approved
0.7414	Intermediate Similarity	NPD7102	Approved
0.7414	Intermediate Similarity	NPD6883	Approved
0.7414	Intermediate Similarity	NPD7290	Approved
0.7387	Intermediate Similarity	NPD7640	Approved
0.7387	Intermediate Similarity	NPD7639	Approved
0.7383	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD6402	Approved
0.7368	Intermediate Similarity	NPD7128	Approved
0.7368	Intermediate Similarity	NPD5739	Approved
0.7368	Intermediate Similarity	NPD6675	Approved
0.735	Intermediate Similarity	NPD8130	Phase 1
0.735	Intermediate Similarity	NPD6650	Approved
0.735	Intermediate Similarity	NPD6649	Approved
0.735	Intermediate Similarity	NPD6869	Approved
0.735	Intermediate Similarity	NPD6847	Approved
0.735	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6013	Approved
0.7328	Intermediate Similarity	NPD6012	Approved
0.7328	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD5779	Approved
0.7315	Intermediate Similarity	NPD5778	Approved
0.7304	Intermediate Similarity	NPD6412	Phase 2
0.7297	Intermediate Similarity	NPD7638	Approved
0.7297	Intermediate Similarity	NPD5696	Approved
0.7288	Intermediate Similarity	NPD6053	Discontinued
0.7288	Intermediate Similarity	NPD6882	Approved
0.7264	Intermediate Similarity	NPD5737	Approved
0.7264	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6672	Approved
0.7257	Intermediate Similarity	NPD5211	Phase 2
0.7248	Intermediate Similarity	NPD7748	Approved
0.7244	Intermediate Similarity	NPD7319	Approved
0.7241	Intermediate Similarity	NPD7320	Approved
0.7241	Intermediate Similarity	NPD6011	Approved
0.7238	Intermediate Similarity	NPD5330	Approved
0.7238	Intermediate Similarity	NPD7146	Approved
0.7238	Intermediate Similarity	NPD7521	Approved
0.7238	Intermediate Similarity	NPD7334	Approved
0.7238	Intermediate Similarity	NPD6409	Approved
0.7238	Intermediate Similarity	NPD6684	Approved
0.7236	Intermediate Similarity	NPD7503	Approved
0.7227	Intermediate Similarity	NPD4632	Approved
0.7222	Intermediate Similarity	NPD5281	Approved
0.7222	Intermediate Similarity	NPD5284	Approved
0.7222	Intermediate Similarity	NPD5693	Phase 1
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7222	Intermediate Similarity	NPD6079	Approved
0.7222	Intermediate Similarity	NPD7637	Suspended
0.7212	Intermediate Similarity	NPD4786	Approved
0.72	Intermediate Similarity	NPD7492	Approved
0.7196	Intermediate Similarity	NPD6101	Approved
0.7196	Intermediate Similarity	NPD4753	Phase 2
0.7196	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5210	Approved
0.7182	Intermediate Similarity	NPD4629	Approved
0.7179	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6372	Approved
0.7179	Intermediate Similarity	NPD6373	Approved
0.7165	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD5701	Approved
0.7155	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD5363	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.7119	Intermediate Similarity	NPD4634	Approved
0.7103	Intermediate Similarity	NPD6903	Approved
0.7087	Intermediate Similarity	NPD7078	Approved
0.708	Intermediate Similarity	NPD5286	Approved
0.708	Intermediate Similarity	NPD4696	Approved
0.708	Intermediate Similarity	NPD5285	Approved
0.7075	Intermediate Similarity	NPD5690	Phase 2
0.7075	Intermediate Similarity	NPD4623	Approved
0.7075	Intermediate Similarity	NPD5279	Phase 3
0.7075	Intermediate Similarity	NPD4519	Discontinued
0.7064	Intermediate Similarity	NPD5694	Approved
0.7064	Intermediate Similarity	NPD6050	Approved
0.7054	Intermediate Similarity	NPD7902	Approved
0.7048	Intermediate Similarity	NPD3133	Approved
0.7048	Intermediate Similarity	NPD3666	Approved
0.7048	Intermediate Similarity	NPD3665	Phase 1
0.704	Intermediate Similarity	NPD6370	Approved
0.7037	Intermediate Similarity	NPD6904	Approved
0.7037	Intermediate Similarity	NPD5328	Approved
0.7037	Intermediate Similarity	NPD6080	Approved
0.7037	Intermediate Similarity	NPD6673	Approved
0.7019	Intermediate Similarity	NPD3667	Approved
0.6972	Remote Similarity	NPD46	Approved
0.6972	Remote Similarity	NPD5692	Phase 3
0.6972	Remote Similarity	NPD5207	Approved
0.6972	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5222	Approved
0.6964	Remote Similarity	NPD5221	Approved
0.6961	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6015	Approved
0.696	Remote Similarity	NPD8513	Phase 3
0.696	Remote Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD5224	Approved
0.6957	Remote Similarity	NPD5225	Approved
0.6957	Remote Similarity	NPD4633	Approved
0.6957	Remote Similarity	NPD5226	Approved
0.6952	Remote Similarity	NPD5362	Discontinued
0.6952	Remote Similarity	NPD7154	Phase 3
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7101	Approved
0.6935	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3618	Phase 1
0.6916	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6009	Approved
0.6905	Remote Similarity	NPD5988	Approved
0.6903	Remote Similarity	NPD5173	Approved
0.6903	Remote Similarity	NPD4755	Approved
0.6897	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD5175	Approved
0.6887	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6051	Approved
0.688	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5223	Approved
0.687	Remote Similarity	NPD5344	Discontinued
0.6857	Remote Similarity	NPD4270	Approved
0.6857	Remote Similarity	NPD4223	Phase 3
0.6857	Remote Similarity	NPD4269	Approved
0.6857	Remote Similarity	NPD4221	Approved
0.6855	Remote Similarity	NPD6335	Approved
0.6855	Remote Similarity	NPD7327	Approved
0.6855	Remote Similarity	NPD7328	Approved
0.6852	Remote Similarity	NPD3573	Approved
0.685	Remote Similarity	NPD7604	Phase 2
0.6847	Remote Similarity	NPD4202	Approved
0.6833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6274	Approved
0.6829	Remote Similarity	NPD6868	Approved
0.6825	Remote Similarity	NPD8515	Approved
0.6825	Remote Similarity	NPD8517	Approved
0.6825	Remote Similarity	NPD8516	Approved
0.6825	Remote Similarity	NPD5983	Phase 2
0.6825	Remote Similarity	NPD8033	Approved
0.6822	Remote Similarity	NPD8293	Discontinued
0.6822	Remote Similarity	NPD5329	Approved
0.681	Remote Similarity	NPD7632	Discontinued
0.68	Remote Similarity	NPD7516	Approved
0.6789	Remote Similarity	NPD5208	Approved
0.6786	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7900	Approved
0.6783	Remote Similarity	NPD4700	Approved
0.6783	Remote Similarity	NPD6404	Discontinued
0.6774	Remote Similarity	NPD6317	Approved
0.6762	Remote Similarity	NPD5369	Approved
0.6759	Remote Similarity	NPD6098	Approved
0.6759	Remote Similarity	NPD5280	Approved
0.6759	Remote Similarity	NPD4694	Approved
0.6759	Remote Similarity	NPD5786	Approved
0.6757	Remote Similarity	NPD7983	Approved
0.6746	Remote Similarity	NPD8377	Approved
0.6746	Remote Similarity	NPD8294	Approved
0.6744	Remote Similarity	NPD6336	Discontinued
0.6742	Remote Similarity	NPD7260	Phase 2
0.6729	Remote Similarity	NPD4197	Approved
0.672	Remote Similarity	NPD6313	Approved
0.672	Remote Similarity	NPD6314	Approved
0.6719	Remote Similarity	NPD8328	Phase 3
0.6698	Remote Similarity	NPD5209	Approved
0.6697	Remote Similarity	NPD7524	Approved
0.6693	Remote Similarity	NPD8335	Approved
0.6693	Remote Similarity	NPD8380	Approved
0.6693	Remote Similarity	NPD8296	Approved
0.6693	Remote Similarity	NPD8379	Approved
0.6693	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD4522	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