NPASS Compound

Structure

CID27918 OpenBabel06191715352D 37 41 0 0 1 0 0 0 0 0999 V2000 5.6037 4.5439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1122 0.9602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1123 1.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5009 -0.0915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7105 -0.6658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 1.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7243 -0.9955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8778 0.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2675 -0.7910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5406 -0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3876 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2392 -0.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8465 -1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 2.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 2.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0906 0.8921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8773 3.8897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8470 -0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6936 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8471 1.4672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3876 0.9784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2341 2.4446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6366 0.2037 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6936 0.9784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2344 1.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6083 0.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5406 1.4675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8465 -0.4887 0.0000 C 0 0 2 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 3.9475 4.1916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8471 2.4696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0058 1.1985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0623 0.9942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0806 2.9335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 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 7 31 1 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 23 1 0 0 0 0 17 32 1 0 0 0 0 18 20 1 0 0 0 0 18 36 1 0 0 0 0 19 33 2 0 0 0 0 19 37 1 0 0 0 0 20 9 1 1 0 0 0 20 21 1 0 0 0 0 21 32 1 6 0 0 0 22 27 2 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 34 1 1 0 0 0 24 28 1 0 0 0 0 24 30 1 6 0 0 0 25 28 1 0 0 0 0 25 37 1 6 0 0 0 26 29 1 6 0 0 0 26 36 1 0 0 0 0 27 30 1 0 0 0 0 29 35 1 0 0 0 0 30 6 1 6 0 0 0 31 32 1 1 0 0 0 32 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.38
Volume:	557.924
LogP:	5.382
LogD:	4.195
LogS:	-5.085
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	5.157
Fsp3:	0.906
Lipinski Rule-of-5:	Rejected
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:	-5.008
MDCK Permeability:	2.1269946955726482e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	92.37154388427734%
Volume Distribution (VD):	1.107
Pgp-substrate:	1.975877046585083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.306
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.506
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.685

ADMET: Excretion

Clearance (CL):	3.296
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.746
Drug-inuced Liver Injury (DILI):	0.791
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.923
Carcinogencity:	0.032
Eye Corrosion:	0.083
Eye Irritation:	0.093
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC27918

Natural Product ID:	NPC27918
*Common Name:**	Hypocrellol D
IUPAC Name:	[(3S,5R,10S,11R,13R,14R,17R)-11-hydroxy-17-[(3R,6R)-6-(2-hydroxypropan-2-yl)oxan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Hypocrellol D
Standard InCHIKey:	FGFAOYBESHLCOZ-ITVSTCJBSA-N
Standard InCHI:	InChI=1S/C32H52O5/c1-19(33)37-25-14-15-30(6)24(28(25,2)3)11-10-22-27(30)23(34)17-32(8)21(13-16-31(22,32)7)20-9-12-26(36-18-20)29(4,5)35/h20-21,23-26,34-35H,9-18H2,1-8H3/t20-,21+,23+,24-,25-,26+,30-,31-,32+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CCC3=C2[C@@H](C[C@]2(C)[C@H](CC[C@@]32C)[C@H]2CC[C@H](C(C)(C)O)OC2)O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928579
PubChem CID:	56602269
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
NPO30117	Hypocrella	Genus	Clavicipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21995505]
NPO33604	Hypocrella sp. BCC 14524	Species	Clavicipitaceae	Eukaryota	n.a.	The fungus used in this study was isolated from a scale insect collected in Nam Nao National Park, Phetcha Bun Province, Thailand	n.a.	PMID[21995505]

☑ 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	5
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	30000.0	nM	PMID[456110]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	15000.0	nM	PMID[456110]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	18000.0	nM	PMID[456110]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	38000.0	nM	PMID[456110]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	8000.0	nM	PMID[456110]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[456110]

☑ 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 NPC27918 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	187
0.1-0.2	1483
0.2-0.3	5085
0.3-0.4	14903
0.4-0.5	7961
0.5-0.6	5415
0.6-0.7	5825
0.7-0.8	1765
0.8-0.85	65
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC473269
0.8602	High Similarity	NPC474922
0.8556	High Similarity	NPC245004
0.8542	High Similarity	NPC230546
0.8542	High Similarity	NPC473510
0.8526	High Similarity	NPC210337
0.8421	Intermediate Similarity	NPC88009
0.837	Intermediate Similarity	NPC20946
0.8333	Intermediate Similarity	NPC141401
0.8315	Intermediate Similarity	NPC132635
0.8298	Intermediate Similarity	NPC38232
0.8283	Intermediate Similarity	NPC473523
0.828	Intermediate Similarity	NPC469400
0.828	Intermediate Similarity	NPC20388
0.8247	Intermediate Similarity	NPC247233
0.8247	Intermediate Similarity	NPC470068
0.8242	Intermediate Similarity	NPC474970
0.8242	Intermediate Similarity	NPC168231
0.8229	Intermediate Similarity	NPC7124
0.8229	Intermediate Similarity	NPC54248
0.8229	Intermediate Similarity	NPC276103
0.82	Intermediate Similarity	NPC473543
0.8191	Intermediate Similarity	NPC177641
0.8191	Intermediate Similarity	NPC41239
0.819	Intermediate Similarity	NPC220293
0.8182	Intermediate Similarity	NPC296879
0.8182	Intermediate Similarity	NPC22403
0.8182	Intermediate Similarity	NPC471119
0.8172	Intermediate Similarity	NPC474889
0.8152	Intermediate Similarity	NPC131329
0.8105	Intermediate Similarity	NPC137461
0.8105	Intermediate Similarity	NPC214697
0.81	Intermediate Similarity	NPC324001
0.81	Intermediate Similarity	NPC55954
0.81	Intermediate Similarity	NPC218513
0.81	Intermediate Similarity	NPC474124
0.8085	Intermediate Similarity	NPC148414
0.8085	Intermediate Similarity	NPC175628
0.8085	Intermediate Similarity	NPC111585
0.8081	Intermediate Similarity	NPC470054
0.8081	Intermediate Similarity	NPC155974
0.8081	Intermediate Similarity	NPC475617
0.8065	Intermediate Similarity	NPC280556
0.8061	Intermediate Similarity	NPC92275
0.8061	Intermediate Similarity	NPC476895
0.8058	Intermediate Similarity	NPC477069
0.8058	Intermediate Similarity	NPC477070
0.8022	Intermediate Similarity	NPC15534
0.8021	Intermediate Similarity	NPC471720
0.8021	Intermediate Similarity	NPC215700
0.8021	Intermediate Similarity	NPC184870
0.8021	Intermediate Similarity	NPC469406
0.802	Intermediate Similarity	NPC152966
0.8	Intermediate Similarity	NPC87489
0.8	Intermediate Similarity	NPC26888
0.8	Intermediate Similarity	NPC470053
0.8	Intermediate Similarity	NPC475344
0.8	Intermediate Similarity	NPC212948
0.8	Intermediate Similarity	NPC476471
0.8	Intermediate Similarity	NPC7988
0.8	Intermediate Similarity	NPC281702
0.8	Intermediate Similarity	NPC469316
0.7981	Intermediate Similarity	NPC90630
0.7981	Intermediate Similarity	NPC475243
0.798	Intermediate Similarity	NPC307954
0.798	Intermediate Similarity	NPC208358
0.7979	Intermediate Similarity	NPC262858
0.7979	Intermediate Similarity	NPC472240
0.7961	Intermediate Similarity	NPC472218
0.7961	Intermediate Similarity	NPC472219
0.7961	Intermediate Similarity	NPC472217
0.7961	Intermediate Similarity	NPC195708
0.7959	Intermediate Similarity	NPC476893
0.7959	Intermediate Similarity	NPC475032
0.7959	Intermediate Similarity	NPC475033
0.7957	Intermediate Similarity	NPC138756
0.7944	Intermediate Similarity	NPC146652
0.7941	Intermediate Similarity	NPC473199
0.7938	Intermediate Similarity	NPC180557
0.7938	Intermediate Similarity	NPC476894
0.7938	Intermediate Similarity	NPC69548
0.7938	Intermediate Similarity	NPC469329
0.7938	Intermediate Similarity	NPC30677
0.7938	Intermediate Similarity	NPC37787
0.7938	Intermediate Similarity	NPC473415
0.7938	Intermediate Similarity	NPC184848
0.7935	Intermediate Similarity	NPC16350
0.7935	Intermediate Similarity	NPC35933
0.7935	Intermediate Similarity	NPC308041
0.7917	Intermediate Similarity	NPC470254
0.7912	Intermediate Similarity	NPC474634
0.7912	Intermediate Similarity	NPC5280
0.7905	Intermediate Similarity	NPC477073
0.79	Intermediate Similarity	NPC235920
0.79	Intermediate Similarity	NPC96784
0.79	Intermediate Similarity	NPC476896
0.7895	Intermediate Similarity	NPC472307
0.7895	Intermediate Similarity	NPC471896
0.7889	Intermediate Similarity	NPC70927
0.7889	Intermediate Similarity	NPC6707
0.7885	Intermediate Similarity	NPC265655
0.7885	Intermediate Similarity	NPC284828
0.7885	Intermediate Similarity	NPC5475
0.7885	Intermediate Similarity	NPC475364
0.7885	Intermediate Similarity	NPC472216
0.7885	Intermediate Similarity	NPC173905
0.7879	Intermediate Similarity	NPC300179
0.7879	Intermediate Similarity	NPC470067
0.7879	Intermediate Similarity	NPC470066
0.7879	Intermediate Similarity	NPC102426
0.7879	Intermediate Similarity	NPC275865
0.7872	Intermediate Similarity	NPC242864
0.7857	Intermediate Similarity	NPC304899
0.7857	Intermediate Similarity	NPC129569
0.7857	Intermediate Similarity	NPC253115
0.7857	Intermediate Similarity	NPC120708
0.7857	Intermediate Similarity	NPC190713
0.7849	Intermediate Similarity	NPC28252
0.7849	Intermediate Similarity	NPC475069
0.7849	Intermediate Similarity	NPC175145
0.7849	Intermediate Similarity	NPC55309
0.7849	Intermediate Similarity	NPC125399
0.7843	Intermediate Similarity	NPC470768
0.7843	Intermediate Similarity	NPC75608
0.7843	Intermediate Similarity	NPC85593
0.7843	Intermediate Similarity	NPC31430
0.7835	Intermediate Similarity	NPC119562
0.7835	Intermediate Similarity	NPC240617
0.7835	Intermediate Similarity	NPC279410
0.7826	Intermediate Similarity	NPC231310
0.7826	Intermediate Similarity	NPC474047
0.7826	Intermediate Similarity	NPC185568
0.7812	Intermediate Similarity	NPC471453
0.7812	Intermediate Similarity	NPC107690
0.7812	Intermediate Similarity	NPC189520
0.7812	Intermediate Similarity	NPC234335
0.781	Intermediate Similarity	NPC129340
0.7802	Intermediate Similarity	NPC256112
0.7802	Intermediate Similarity	NPC202389
0.7802	Intermediate Similarity	NPC30166
0.78	Intermediate Similarity	NPC144660
0.78	Intermediate Similarity	NPC299971
0.7791	Intermediate Similarity	NPC201373
0.7789	Intermediate Similarity	NPC16265
0.7789	Intermediate Similarity	NPC246028
0.7789	Intermediate Similarity	NPC146554
0.7788	Intermediate Similarity	NPC38217
0.7788	Intermediate Similarity	NPC472988
0.7778	Intermediate Similarity	NPC122294
0.7778	Intermediate Similarity	NPC206735
0.7778	Intermediate Similarity	NPC320306
0.7778	Intermediate Similarity	NPC231751
0.7778	Intermediate Similarity	NPC261807
0.7778	Intermediate Similarity	NPC121339
0.7767	Intermediate Similarity	NPC475494
0.7767	Intermediate Similarity	NPC472899
0.7767	Intermediate Similarity	NPC472900
0.7767	Intermediate Similarity	NPC323834
0.7767	Intermediate Similarity	NPC470763
0.7767	Intermediate Similarity	NPC472898
0.7767	Intermediate Similarity	NPC470767
0.7766	Intermediate Similarity	NPC187376
0.7766	Intermediate Similarity	NPC159046
0.7766	Intermediate Similarity	NPC470620
0.7766	Intermediate Similarity	NPC233836
0.7766	Intermediate Similarity	NPC166857
0.7757	Intermediate Similarity	NPC477074
0.7755	Intermediate Similarity	NPC474909
0.7755	Intermediate Similarity	NPC473648
0.7755	Intermediate Similarity	NPC86893
0.7755	Intermediate Similarity	NPC292178
0.7755	Intermediate Similarity	NPC279974
0.7745	Intermediate Similarity	NPC475623
0.7745	Intermediate Similarity	NPC475334
0.7745	Intermediate Similarity	NPC85742
0.7745	Intermediate Similarity	NPC473694
0.7742	Intermediate Similarity	NPC191965
0.7736	Intermediate Similarity	NPC292196
0.7732	Intermediate Similarity	NPC53555
0.7732	Intermediate Similarity	NPC476304
0.7727	Intermediate Similarity	NPC73875
0.7723	Intermediate Similarity	NPC289670
0.7723	Intermediate Similarity	NPC21064
0.7723	Intermediate Similarity	NPC121072
0.7723	Intermediate Similarity	NPC470434
0.7723	Intermediate Similarity	NPC476897
0.7717	Intermediate Similarity	NPC317458
0.7717	Intermediate Similarity	NPC476927
0.7714	Intermediate Similarity	NPC43976
0.7714	Intermediate Similarity	NPC125361
0.7714	Intermediate Similarity	NPC51925
0.7714	Intermediate Similarity	NPC41405
0.7714	Intermediate Similarity	NPC296761
0.7714	Intermediate Similarity	NPC154085
0.7708	Intermediate Similarity	NPC477147
0.7708	Intermediate Similarity	NPC136801
0.7708	Intermediate Similarity	NPC289213
0.7708	Intermediate Similarity	NPC477149
0.77	Intermediate Similarity	NPC16021
0.77	Intermediate Similarity	NPC303777

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 NPC27918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1776
0.2-0.3	4074
0.3-0.4	2208
0.4-0.5	479
0.5-0.6	190
0.6-0.7	222
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7391	Intermediate Similarity	NPD7525	Registered
0.7353	Intermediate Similarity	NPD7638	Approved
0.7345	Intermediate Similarity	NPD8377	Approved
0.7345	Intermediate Similarity	NPD8294	Approved
0.7321	Intermediate Similarity	NPD7327	Approved
0.7321	Intermediate Similarity	NPD7328	Approved
0.7308	Intermediate Similarity	NPD7632	Discontinued
0.7281	Intermediate Similarity	NPD8033	Approved
0.7281	Intermediate Similarity	NPD8296	Approved
0.7281	Intermediate Similarity	NPD8380	Approved
0.7281	Intermediate Similarity	NPD8379	Approved
0.7281	Intermediate Similarity	NPD8378	Approved
0.7281	Intermediate Similarity	NPD8335	Approved
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7257	Intermediate Similarity	NPD7516	Approved
0.7245	Intermediate Similarity	NPD6051	Approved
0.7222	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4748	Discontinued
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7188	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4225	Approved
0.7182	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD7503	Approved
0.7129	Intermediate Similarity	NPD7748	Approved
0.7103	Intermediate Similarity	NPD7128	Approved
0.7103	Intermediate Similarity	NPD5739	Approved
0.7103	Intermediate Similarity	NPD6675	Approved
0.7103	Intermediate Similarity	NPD6402	Approved
0.7064	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7524	Approved
0.7033	Intermediate Similarity	NPD6942	Approved
0.7033	Intermediate Similarity	NPD7339	Approved
0.6972	Remote Similarity	NPD6899	Approved
0.6972	Remote Similarity	NPD6881	Approved
0.6972	Remote Similarity	NPD7320	Approved
0.6937	Remote Similarity	NPD8130	Phase 1
0.6931	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD7902	Approved
0.6915	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD6373	Approved
0.6909	Remote Similarity	NPD6372	Approved
0.6907	Remote Similarity	NPD4786	Approved
0.69	Remote Similarity	NPD5328	Approved
0.6893	Remote Similarity	NPD5695	Phase 3
0.6891	Remote Similarity	NPD7507	Approved
0.6887	Remote Similarity	NPD4159	Approved
0.6881	Remote Similarity	NPD5697	Approved
0.6881	Remote Similarity	NPD5701	Approved
0.6869	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7102	Approved
0.6847	Remote Similarity	NPD6883	Approved
0.6847	Remote Similarity	NPD7290	Approved
0.6818	Remote Similarity	NPD6011	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6814	Remote Similarity	NPD8133	Approved
0.6804	Remote Similarity	NPD6695	Phase 3
0.6786	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6847	Approved
0.6786	Remote Similarity	NPD6650	Approved
0.6786	Remote Similarity	NPD6869	Approved
0.6786	Remote Similarity	NPD6649	Approved
0.6786	Remote Similarity	NPD6617	Approved
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6933	Approved
0.6774	Remote Similarity	NPD6117	Approved
0.6768	Remote Similarity	NPD3618	Phase 1
0.6765	Remote Similarity	NPD6079	Approved
0.6765	Remote Similarity	NPD7637	Suspended
0.6757	Remote Similarity	NPD6014	Approved
0.6757	Remote Similarity	NPD6012	Approved
0.6757	Remote Similarity	NPD6013	Approved
0.6735	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD6882	Approved
0.6721	Remote Similarity	NPD7319	Approved
0.6702	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD3667	Approved
0.67	Remote Similarity	NPD7750	Discontinued
0.6699	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD8264	Approved
0.6638	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7900	Approved
0.6635	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5737	Approved
0.6634	Remote Similarity	NPD6672	Approved
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6697	Approved
0.6632	Remote Similarity	NPD6114	Approved
0.6632	Remote Similarity	NPD6118	Approved
0.6632	Remote Similarity	NPD6115	Approved
0.661	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD4755	Approved
0.6602	Remote Similarity	NPD6411	Approved
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD6684	Approved
0.66	Remote Similarity	NPD5330	Approved
0.66	Remote Similarity	NPD7146	Approved
0.6574	Remote Similarity	NPD5344	Discontinued
0.6571	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6926	Approved
0.6559	Remote Similarity	NPD6924	Approved
0.6545	Remote Similarity	NPD5141	Approved
0.6542	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD4243	Approved
0.6518	Remote Similarity	NPD6686	Approved
0.6509	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5221	Approved
0.6509	Remote Similarity	NPD5222	Approved
0.6509	Remote Similarity	NPD4697	Phase 3
0.6504	Remote Similarity	NPD7736	Approved
0.6496	Remote Similarity	NPD6009	Approved
0.6495	Remote Similarity	NPD6931	Approved
0.6495	Remote Similarity	NPD6930	Phase 2
0.6481	Remote Similarity	NPD4700	Approved
0.6481	Remote Similarity	NPD4696	Approved
0.6481	Remote Similarity	NPD5286	Approved
0.6481	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5173	Approved
0.6446	Remote Similarity	NPD7604	Phase 2
0.6442	Remote Similarity	NPD5284	Approved
0.6442	Remote Similarity	NPD6050	Approved
0.6442	Remote Similarity	NPD5281	Approved
0.6441	Remote Similarity	NPD6335	Approved
0.6436	Remote Similarity	NPD6098	Approved
0.6436	Remote Similarity	NPD5279	Phase 3
0.6429	Remote Similarity	NPD4139	Approved
0.6429	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4692	Approved
0.6423	Remote Similarity	NPD8293	Discontinued
0.6422	Remote Similarity	NPD5223	Approved
0.6417	Remote Similarity	NPD5983	Phase 2
0.641	Remote Similarity	NPD6868	Approved
0.641	Remote Similarity	NPD6274	Approved
0.6408	Remote Similarity	NPD6101	Approved
0.6408	Remote Similarity	NPD6673	Approved
0.6408	Remote Similarity	NPD6080	Approved
0.6408	Remote Similarity	NPD4753	Phase 2
0.6408	Remote Similarity	NPD6904	Approved
0.6408	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3666	Approved
0.64	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD3133	Approved
0.6393	Remote Similarity	NPD7492	Approved
0.6392	Remote Similarity	NPD4195	Approved
0.6392	Remote Similarity	NPD6929	Approved
0.6387	Remote Similarity	NPD7100	Approved
0.6387	Remote Similarity	NPD7101	Approved
0.6383	Remote Similarity	NPD4785	Approved
0.6383	Remote Similarity	NPD4784	Approved
0.6381	Remote Similarity	NPD5779	Approved
0.6381	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD3573	Approved
0.6372	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD6317	Approved
0.6346	Remote Similarity	NPD5692	Phase 3
0.6341	Remote Similarity	NPD6336	Discontinued
0.6341	Remote Similarity	NPD6616	Approved
0.6339	Remote Similarity	NPD6008	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.6333	Remote Similarity	NPD6054	Approved
0.6327	Remote Similarity	NPD7514	Phase 3
0.6316	Remote Similarity	NPD3702	Approved
0.6311	Remote Similarity	NPD8328	Phase 3
0.6306	Remote Similarity	NPD5174	Approved
0.6306	Remote Similarity	NPD4754	Approved
0.6306	Remote Similarity	NPD5175	Approved
0.6303	Remote Similarity	NPD6314	Approved
0.6303	Remote Similarity	NPD6313	Approved
0.63	Remote Similarity	NPD5362	Discontinued
0.629	Remote Similarity	NPD7078	Approved
0.6289	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5694	Approved
0.6286	Remote Similarity	NPD7087	Discontinued
0.6286	Remote Similarity	NPD5693	Phase 1
0.6281	Remote Similarity	NPD6909	Approved
0.6281	Remote Similarity	NPD8513	Phase 3
0.6281	Remote Similarity	NPD8516	Approved
0.6281	Remote Similarity	NPD6908	Approved
0.6281	Remote Similarity	NPD8517	Approved
0.6281	Remote Similarity	NPD8515	Approved
0.6275	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4634	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