NPASS Compound

Structure

NPC470067 OpenBabel07101719252D 38 42 0 0 1 0 0 0 0 0999 V2000 7.2484 -3.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2035 -0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6906 0.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8898 0.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2663 -0.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2759 0.1557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6133 -1.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5684 1.9992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4914 2.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4874 2.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7399 -0.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3601 -1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8664 -0.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4867 -1.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3152 1.0252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1069 -2.9484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 1.4088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0984 1.6313 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 2.1906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7099 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5983 -0.0006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3302 0.0253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4418 1.5122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2185 -1.4616 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1235 1.4088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2036 -0.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8515 0.9734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4717 -0.4876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5833 0.9993 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9803 -3.4354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9339 3.0916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4268 2.5121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0984 1.6313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0919 -1.9485 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 1 0 0 0 0 12 26 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 25 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 1 0 0 0 23 32 1 0 0 0 0 24 28 1 0 0 0 0 24 31 1 1 0 0 0 25 32 1 6 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 38 1 6 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 6 0 0 0 31 7 1 1 0 0 0 32 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.38
Volume:	566.714
LogP:	4.139
LogD:	3.603
LogS:	-4.402
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.341
Synthetic Accessibility Score:	5.3
Fsp3:	0.906
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:	-4.993
MDCK Permeability:	9.129416866926476e-06
Pgp-inhibitor:	0.997
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	88.73709106445312%
Volume Distribution (VD):	1.06
Pgp-substrate:	6.746983528137207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.164
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	2.458
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.11
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.812
Skin Sensitization:	0.603
Carcinogencity:	0.011
Eye Corrosion:	0.005
Eye Irritation:	0.018
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC470067

Natural Product ID:	NPC470067
*Common Name:**	Chisiamol B
IUPAC Name:	[(3R,5R,7R,8R,9R,10S,13S,17R)-17-[(3S,5R,6S)-5,6-dihydroxy-7,7-dimethyloxepan-3-yl]-7-hydroxy-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Chisiamol B
Standard InCHIKey:	QFANNTJTSGTLCA-JRIYAETESA-N
Standard InCHI:	InChI=1S/C32H52O6/c1-18(33)38-26-12-14-31(7)23-11-13-30(6)20(19-15-21(34)27(36)29(4,5)37-17-19)9-10-22(30)32(23,8)25(35)16-24(31)28(26,2)3/h10,19-21,23-27,34-36H,9,11-17H2,1-8H3/t19-,20-,21-,23-,24+,25-,26-,27+,30+,31-,32+/m1/s1
SMILES:	CC(=O)OC1CCC2(C3CCC4(C(CC=C4C3(C(CC2C1(C)C)O)C)C5CC(C(C(OC5)(C)C)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668621
PubChem CID:	53319632
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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16500.0	nM	PMID[538018]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[538018]

☑ 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 NPC470067 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	226
0.1-0.2	1611
0.2-0.3	5051
0.3-0.4	12591
0.4-0.5	9875
0.5-0.6	5791
0.6-0.7	5491
0.7-0.8	1984
0.8-0.85	60
0.85-0.9	13
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470066
0.957	High Similarity	NPC470068
0.9368	High Similarity	NPC470054
0.9271	High Similarity	NPC470053
0.9082	High Similarity	NPC470062
0.9082	High Similarity	NPC470057
0.9082	High Similarity	NPC470059
0.9082	High Similarity	NPC470061
0.9082	High Similarity	NPC470043
0.9082	High Similarity	NPC470060
0.9082	High Similarity	NPC470058
0.9082	High Similarity	NPC470064
0.8824	High Similarity	NPC250956
0.8776	High Similarity	NPC155974
0.8763	High Similarity	NPC102426
0.8763	High Similarity	NPC300179
0.875	High Similarity	NPC471903
0.8723	High Similarity	NPC210268
0.8673	High Similarity	NPC208358
0.866	High Similarity	NPC475032
0.866	High Similarity	NPC475033
0.8654	High Similarity	NPC234042
0.8654	High Similarity	NPC152117
0.8614	High Similarity	NPC470056
0.8614	High Similarity	NPC470055
0.8614	High Similarity	NPC473199
0.8614	High Similarity	NPC472655
0.86	High Similarity	NPC474124
0.8586	High Similarity	NPC475617
0.8586	High Similarity	NPC289670
0.8571	High Similarity	NPC477876
0.8571	High Similarity	NPC477875
0.8557	High Similarity	NPC253115
0.8557	High Similarity	NPC304899
0.8544	High Similarity	NPC218853
0.8529	High Similarity	NPC469318
0.8529	High Similarity	NPC473173
0.8526	High Similarity	NPC219516
0.8515	High Similarity	NPC85593
0.8515	High Similarity	NPC31430
0.8515	High Similarity	NPC473543
0.85	High Similarity	NPC475344
0.85	High Similarity	NPC476471
0.8485	Intermediate Similarity	NPC473510
0.8454	Intermediate Similarity	NPC30677
0.8454	Intermediate Similarity	NPC469329
0.8454	Intermediate Similarity	NPC180557
0.8454	Intermediate Similarity	NPC473415
0.8454	Intermediate Similarity	NPC37787
0.8447	Intermediate Similarity	NPC472988
0.8447	Intermediate Similarity	NPC38217
0.8416	Intermediate Similarity	NPC473523
0.84	Intermediate Similarity	NPC476132
0.8384	Intermediate Similarity	NPC119036
0.8365	Intermediate Similarity	NPC51925
0.8365	Intermediate Similarity	NPC43976
0.8365	Intermediate Similarity	NPC125361
0.8365	Intermediate Similarity	NPC154085
0.8365	Intermediate Similarity	NPC296761
0.835	Intermediate Similarity	NPC234160
0.8317	Intermediate Similarity	NPC136816
0.8302	Intermediate Similarity	NPC470063
0.83	Intermediate Similarity	NPC474571
0.83	Intermediate Similarity	NPC167974
0.83	Intermediate Similarity	NPC476195
0.83	Intermediate Similarity	NPC230546
0.83	Intermediate Similarity	NPC254567
0.8298	Intermediate Similarity	NPC189777
0.8283	Intermediate Similarity	NPC210337
0.8269	Intermediate Similarity	NPC472218
0.8269	Intermediate Similarity	NPC472217
0.8269	Intermediate Similarity	NPC472219
0.8265	Intermediate Similarity	NPC279974
0.8265	Intermediate Similarity	NPC86893
0.8265	Intermediate Similarity	NPC292178
0.8235	Intermediate Similarity	NPC475334
0.8235	Intermediate Similarity	NPC473694
0.8235	Intermediate Similarity	NPC475623
0.8229	Intermediate Similarity	NPC473269
0.8229	Intermediate Similarity	NPC10274
0.8218	Intermediate Similarity	NPC309425
0.8218	Intermediate Similarity	NPC235920
0.8218	Intermediate Similarity	NPC160734
0.8218	Intermediate Similarity	NPC129372
0.8218	Intermediate Similarity	NPC4831
0.8218	Intermediate Similarity	NPC96784
0.8218	Intermediate Similarity	NPC472023
0.8218	Intermediate Similarity	NPC88000
0.8218	Intermediate Similarity	NPC47566
0.8208	Intermediate Similarity	NPC114188
0.8208	Intermediate Similarity	NPC470076
0.8208	Intermediate Similarity	NPC65167
0.82	Intermediate Similarity	NPC234287
0.82	Intermediate Similarity	NPC280825
0.82	Intermediate Similarity	NPC247233
0.82	Intermediate Similarity	NPC476895
0.8191	Intermediate Similarity	NPC474970
0.819	Intermediate Similarity	NPC284828
0.819	Intermediate Similarity	NPC173905
0.819	Intermediate Similarity	NPC472216
0.819	Intermediate Similarity	NPC5475
0.8182	Intermediate Similarity	NPC475304
0.8182	Intermediate Similarity	NPC88009
0.8182	Intermediate Similarity	NPC475178
0.8182	Intermediate Similarity	NPC471777
0.8182	Intermediate Similarity	NPC54248
0.8182	Intermediate Similarity	NPC276103
0.8172	Intermediate Similarity	NPC299963
0.8163	Intermediate Similarity	NPC474922
0.8163	Intermediate Similarity	NPC211238
0.8155	Intermediate Similarity	NPC288502
0.8155	Intermediate Similarity	NPC181104
0.8155	Intermediate Similarity	NPC475331
0.8155	Intermediate Similarity	NPC121518
0.8155	Intermediate Similarity	NPC475335
0.8155	Intermediate Similarity	NPC475585
0.8155	Intermediate Similarity	NPC474550
0.8155	Intermediate Similarity	NPC201144
0.8155	Intermediate Similarity	NPC80809
0.8155	Intermediate Similarity	NPC103298
0.8155	Intermediate Similarity	NPC473577
0.8144	Intermediate Similarity	NPC473166
0.8137	Intermediate Similarity	NPC154452
0.8119	Intermediate Similarity	NPC7341
0.8119	Intermediate Similarity	NPC38855
0.8119	Intermediate Similarity	NPC473200
0.8113	Intermediate Similarity	NPC475563
0.8113	Intermediate Similarity	NPC470065
0.8113	Intermediate Similarity	NPC475134
0.8113	Intermediate Similarity	NPC101450
0.8113	Intermediate Similarity	NPC5284
0.81	Intermediate Similarity	NPC272451
0.81	Intermediate Similarity	NPC476893
0.81	Intermediate Similarity	NPC254121
0.8095	Intermediate Similarity	NPC258323
0.8085	Intermediate Similarity	NPC290731
0.8077	Intermediate Similarity	NPC220217
0.8077	Intermediate Similarity	NPC470587
0.8077	Intermediate Similarity	NPC119855
0.8077	Intermediate Similarity	NPC472898
0.8077	Intermediate Similarity	NPC477877
0.8077	Intermediate Similarity	NPC60315
0.8077	Intermediate Similarity	NPC472900
0.8077	Intermediate Similarity	NPC475290
0.8077	Intermediate Similarity	NPC472899
0.8061	Intermediate Similarity	NPC473678
0.8058	Intermediate Similarity	NPC31907
0.8058	Intermediate Similarity	NPC114874
0.8058	Intermediate Similarity	NPC155010
0.8058	Intermediate Similarity	NPC472252
0.8058	Intermediate Similarity	NPC222153
0.8058	Intermediate Similarity	NPC120123
0.8058	Intermediate Similarity	NPC473020
0.8058	Intermediate Similarity	NPC218513
0.8058	Intermediate Similarity	NPC211879
0.8058	Intermediate Similarity	NPC157659
0.8058	Intermediate Similarity	NPC189852
0.8058	Intermediate Similarity	NPC472821
0.8058	Intermediate Similarity	NPC131479
0.8058	Intermediate Similarity	NPC8039
0.8058	Intermediate Similarity	NPC473198
0.8058	Intermediate Similarity	NPC286969
0.8058	Intermediate Similarity	NPC245280
0.8058	Intermediate Similarity	NPC55954
0.8058	Intermediate Similarity	NPC16520
0.8058	Intermediate Similarity	NPC213190
0.8056	Intermediate Similarity	NPC255017
0.8056	Intermediate Similarity	NPC144068
0.8039	Intermediate Similarity	NPC11974
0.8039	Intermediate Similarity	NPC21064
0.8039	Intermediate Similarity	NPC476896
0.8039	Intermediate Similarity	NPC121072
0.8037	Intermediate Similarity	NPC475480
0.8037	Intermediate Similarity	NPC475668
0.8037	Intermediate Similarity	NPC473921
0.802	Intermediate Similarity	NPC477928
0.802	Intermediate Similarity	NPC218107
0.802	Intermediate Similarity	NPC5358
0.802	Intermediate Similarity	NPC216260
0.8019	Intermediate Similarity	NPC41405
0.8	Intermediate Similarity	NPC473586
0.8	Intermediate Similarity	NPC155531
0.8	Intermediate Similarity	NPC215968
0.8	Intermediate Similarity	NPC306797
0.8	Intermediate Similarity	NPC214315
0.8	Intermediate Similarity	NPC129569
0.8	Intermediate Similarity	NPC227583
0.8	Intermediate Similarity	NPC292718
0.8	Intermediate Similarity	NPC169270
0.8	Intermediate Similarity	NPC98457
0.8	Intermediate Similarity	NPC111834
0.8	Intermediate Similarity	NPC12103
0.8	Intermediate Similarity	NPC59530
0.7981	Intermediate Similarity	NPC471293
0.7981	Intermediate Similarity	NPC187400
0.7981	Intermediate Similarity	NPC470885
0.7981	Intermediate Similarity	NPC273879
0.7981	Intermediate Similarity	NPC173583
0.7981	Intermediate Similarity	NPC221562
0.7981	Intermediate Similarity	NPC165033

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 NPC470067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1861
0.2-0.3	3998
0.3-0.4	2097
0.4-0.5	590
0.5-0.6	244
0.6-0.7	150
0.7-0.8	22
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
0.7742	Intermediate Similarity	NPD7525	Registered
0.7719	Intermediate Similarity	NPD8033	Approved
0.767	Intermediate Similarity	NPD7638	Approved
0.7632	Intermediate Similarity	NPD8294	Approved
0.7632	Intermediate Similarity	NPD8377	Approved
0.7611	Intermediate Similarity	NPD7328	Approved
0.7611	Intermediate Similarity	NPD7327	Approved
0.7596	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD8380	Approved
0.7565	Intermediate Similarity	NPD8335	Approved
0.7565	Intermediate Similarity	NPD8378	Approved
0.7565	Intermediate Similarity	NPD8296	Approved
0.7565	Intermediate Similarity	NPD8379	Approved
0.7544	Intermediate Similarity	NPD7516	Approved
0.7374	Intermediate Similarity	NPD7524	Approved
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.7321	Intermediate Similarity	NPD8297	Approved
0.7257	Intermediate Similarity	NPD4632	Approved
0.7255	Intermediate Similarity	NPD8034	Phase 2
0.7255	Intermediate Similarity	NPD8035	Phase 2
0.7248	Intermediate Similarity	NPD7128	Approved
0.7248	Intermediate Similarity	NPD6675	Approved
0.7248	Intermediate Similarity	NPD6402	Approved
0.7248	Intermediate Similarity	NPD5739	Approved
0.7245	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6319	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.713	Intermediate Similarity	NPD7632	Discontinued
0.7119	Intermediate Similarity	NPD7503	Approved
0.7117	Intermediate Similarity	NPD7320	Approved
0.7117	Intermediate Similarity	NPD6899	Approved
0.7117	Intermediate Similarity	NPD6881	Approved
0.7115	Intermediate Similarity	NPD7748	Approved
0.7105	Intermediate Similarity	NPD8133	Approved
0.7083	Intermediate Similarity	NPD7645	Phase 2
0.708	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD7902	Approved
0.7069	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7054	Intermediate Similarity	NPD6373	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7037	Intermediate Similarity	NPD5344	Discontinued
0.703	Intermediate Similarity	NPD7750	Discontinued
0.7027	Intermediate Similarity	NPD5697	Approved
0.7027	Intermediate Similarity	NPD5701	Approved
0.7027	Intermediate Similarity	NPD6412	Phase 2
0.7021	Intermediate Similarity	NPD7339	Approved
0.7021	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD7102	Approved
0.6991	Remote Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD7290	Approved
0.6967	Remote Similarity	NPD8293	Discontinued
0.6964	Remote Similarity	NPD6686	Approved
0.6964	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6933	Approved
0.6942	Remote Similarity	NPD7492	Approved
0.6937	Remote Similarity	NPD6008	Approved
0.693	Remote Similarity	NPD6869	Approved
0.693	Remote Similarity	NPD6847	Approved
0.693	Remote Similarity	NPD6617	Approved
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD7637	Suspended
0.6916	Remote Similarity	NPD6083	Phase 2
0.6916	Remote Similarity	NPD6084	Phase 2
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6014	Approved
0.69	Remote Similarity	NPD4786	Approved
0.6891	Remote Similarity	NPD6059	Approved
0.6891	Remote Similarity	NPD6054	Approved
0.6885	Remote Similarity	NPD6616	Approved
0.687	Remote Similarity	NPD6882	Approved
0.686	Remote Similarity	NPD8328	Phase 3
0.686	Remote Similarity	NPD7604	Phase 2
0.6848	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7509	Discontinued
0.6837	Remote Similarity	NPD6930	Phase 2
0.6837	Remote Similarity	NPD6931	Approved
0.6833	Remote Similarity	NPD5983	Phase 2
0.6829	Remote Similarity	NPD7078	Approved
0.6814	Remote Similarity	NPD6011	Approved
0.6804	Remote Similarity	NPD6114	Approved
0.6804	Remote Similarity	NPD6697	Approved
0.6804	Remote Similarity	NPD6118	Approved
0.6804	Remote Similarity	NPD6115	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6370	Approved
0.6771	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4755	Approved
0.6748	Remote Similarity	NPD6336	Discontinued
0.6737	Remote Similarity	NPD6926	Approved
0.6737	Remote Similarity	NPD6924	Approved
0.6735	Remote Similarity	NPD6929	Approved
0.6731	Remote Similarity	NPD6051	Approved
0.6731	Remote Similarity	NPD5328	Approved
0.6724	Remote Similarity	NPD6053	Discontinued
0.6701	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD6932	Approved
0.67	Remote Similarity	NPD3667	Approved
0.6699	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6639	Remote Similarity	NPD5988	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD6648	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6604	Remote Similarity	NPD6079	Approved
0.6604	Remote Similarity	NPD7087	Discontinued
0.6602	Remote Similarity	NPD3618	Phase 1
0.66	Remote Similarity	NPD6898	Phase 1
0.6598	Remote Similarity	NPD6117	Approved
0.6579	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5695	Phase 3
0.6566	Remote Similarity	NPD6683	Phase 2
0.6555	Remote Similarity	NPD6274	Approved
0.6552	Remote Similarity	NPD6371	Approved
0.6545	Remote Similarity	NPD5696	Approved
0.6542	Remote Similarity	NPD8171	Discontinued
0.6531	Remote Similarity	NPD5776	Phase 2
0.6531	Remote Similarity	NPD6925	Approved
0.6529	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD7100	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5211	Phase 2
0.6518	Remote Similarity	NPD4633	Approved
0.6509	Remote Similarity	NPD7838	Discovery
0.6505	Remote Similarity	NPD6893	Approved
0.65	Remote Similarity	NPD4748	Discontinued
0.65	Remote Similarity	NPD7514	Phase 3
0.6476	Remote Similarity	NPD6672	Approved
0.6476	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5737	Approved
0.6465	Remote Similarity	NPD7145	Approved
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6449	Remote Similarity	NPD6411	Approved
0.6446	Remote Similarity	NPD6335	Approved
0.6442	Remote Similarity	NPD5330	Approved
0.6442	Remote Similarity	NPD6409	Approved
0.6442	Remote Similarity	NPD7334	Approved
0.6442	Remote Similarity	NPD6684	Approved
0.6442	Remote Similarity	NPD7146	Approved
0.6442	Remote Similarity	NPD7521	Approved
0.6435	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD6908	Approved
0.6423	Remote Similarity	NPD6909	Approved
0.6422	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4753	Phase 2
0.6404	Remote Similarity	NPD5141	Approved
0.6392	Remote Similarity	NPD4785	Approved
0.6392	Remote Similarity	NPD4784	Approved
0.6392	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6033	Approved
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6355	Remote Similarity	NPD3168	Discontinued
0.6355	Remote Similarity	NPD46	Approved
0.6355	Remote Similarity	NPD6698	Approved
0.6354	Remote Similarity	NPD7150	Approved
0.6354	Remote Similarity	NPD7152	Approved
0.6354	Remote Similarity	NPD4243	Approved
0.6354	Remote Similarity	NPD7151	Approved
0.6348	Remote Similarity	NPD4767	Approved
0.6348	Remote Similarity	NPD4768	Approved
0.6337	Remote Similarity	NPD6928	Phase 2
0.6321	Remote Similarity	NPD6903	Approved
0.632	Remote Similarity	NPD6067	Discontinued
0.6316	Remote Similarity	NPD6922	Approved
0.6316	Remote Similarity	NPD6923	Approved
0.6316	Remote Similarity	NPD4754	Approved
0.6311	Remote Similarity	NPD6313	Approved
0.6311	Remote Similarity	NPD6314	Approved
0.6306	Remote Similarity	NPD5173	Approved
0.63	Remote Similarity	NPD7322	Clinical (unspecified phase)

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