NPASS Compound

Structure

NPC470053 OpenBabel07101718322D 42 46 0 0 1 0 0 0 0 0999 V2000 -7.3386 3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4726 -3.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3386 0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8386 -0.0638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5983 -0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9292 -0.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4207 0.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7405 1.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7405 -1.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6720 -2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6666 -2.1759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4726 2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6065 1.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4726 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2046 3.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4726 -2.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2653 -1.3669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8745 -1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7405 0.3023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4726 0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3386 1.8023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6065 -1.1977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3386 0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6202 -1.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 -0.6977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6065 0.8023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7405 -0.6977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0706 3.8023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3386 -2.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0292 -2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8281 -2.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4123 -0.0740 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 -8.2046 2.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6065 -2.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 26 1 0 0 0 0 17 25 1 0 0 0 0 17 28 1 0 0 0 0 18 21 1 0 0 0 0 18 40 1 0 0 0 0 19 35 2 0 0 0 0 19 41 1 0 0 0 0 20 36 2 0 0 0 0 20 42 1 0 0 0 0 21 16 1 1 0 0 0 21 22 1 0 0 0 0 22 31 1 1 0 0 0 23 31 1 0 0 0 0 23 33 1 0 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 29 1 0 0 0 0 25 32 1 1 0 0 0 26 34 1 6 0 0 0 26 37 1 0 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 33 1 6 0 0 0 28 42 1 0 0 0 0 30 34 1 0 0 0 0 30 38 1 0 0 0 0 31 7 1 6 0 0 0 32 8 1 1 0 0 0 33 9 1 1 0 0 0 34 39 1 1 0 0 0 34 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.38
Volume:	616.25
LogP:	3.932
LogD:	3.281
LogS:	-4.207
# Rotatable Bonds:	6
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	5.464
Fsp3:	0.882
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:	-5.24
MDCK Permeability:	3.3946729672607034e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.693

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	85.89405059814453%
Volume Distribution (VD):	0.902
Pgp-substrate:	8.154403686523438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.717
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	2.254
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.305
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.295
Skin Sensitization:	0.21
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC470053

Natural Product ID:	NPC470053
*Common Name:**	Chisopanin A
IUPAC Name:	[(3R,5R,7R,8R,9R,10S,13S,17R)-7-acetyloxy-17-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-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:	Chisopanin A
Standard InCHIKey:	VSHMLGFPIOVLBX-ZFNCJFMFSA-N
Standard InCHI:	InChI=1S/C34H54O8/c1-19(35)41-27-13-15-32(8)24-12-14-31(7)22(21-16-26(37)34(39,40-18-21)30(5,6)38)10-11-23(31)33(24,9)28(42-20(2)36)17-25(32)29(27,3)4/h11,21-22,24-28,37-39H,10,12-18H2,1-9H3/t21-,22-,24-,25+,26-,27-,28-,31+,32-,33+,34+/m1/s1
SMILES:	CC(=O)OC1CCC2(C3CCC4(C(CC=C4C3(C(CC2C1(C)C)OC(=O)C)C)C5CC(C(OC5)(C(C)(C)O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668606
PubChem CID:	53326180
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	=	5400.0	nM	PMID[535833]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	26900.0	nM	PMID[535833]

☑ 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 NPC470053 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	235
0.1-0.2	1700
0.2-0.3	5055
0.3-0.4	12116
0.4-0.5	10363
0.5-0.6	5583
0.6-0.7	4563
0.7-0.8	2471
0.8-0.85	556
0.85-0.9	52
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC470054
0.9681	High Similarity	NPC470068
0.9293	High Similarity	NPC473199
0.9271	High Similarity	NPC470067
0.9271	High Similarity	NPC470066
0.9192	High Similarity	NPC470061
0.9192	High Similarity	NPC470064
0.9192	High Similarity	NPC470058
0.9192	High Similarity	NPC470062
0.9192	High Similarity	NPC470059
0.9192	High Similarity	NPC470060
0.9192	High Similarity	NPC470043
0.9192	High Similarity	NPC470057
0.9109	High Similarity	NPC38217
0.9109	High Similarity	NPC472988
0.902	High Similarity	NPC51925
0.902	High Similarity	NPC218853
0.902	High Similarity	NPC296761
0.902	High Similarity	NPC125361
0.902	High Similarity	NPC154085
0.902	High Similarity	NPC43976
0.901	High Similarity	NPC234160
0.899	High Similarity	NPC136816
0.8932	High Similarity	NPC250956
0.8889	High Similarity	NPC472023
0.8889	High Similarity	NPC309425
0.8889	High Similarity	NPC160734
0.8889	High Similarity	NPC88000
0.8889	High Similarity	NPC129372
0.8889	High Similarity	NPC47566
0.8889	High Similarity	NPC4831
0.8846	High Similarity	NPC114188
0.8846	High Similarity	NPC65167
0.8788	High Similarity	NPC7341
0.8788	High Similarity	NPC473200
0.8725	High Similarity	NPC472898
0.8725	High Similarity	NPC470055
0.8725	High Similarity	NPC470056
0.8725	High Similarity	NPC472900
0.8725	High Similarity	NPC472899
0.8713	High Similarity	NPC114874
0.8713	High Similarity	NPC155010
0.8713	High Similarity	NPC31907
0.8713	High Similarity	NPC8039
0.8713	High Similarity	NPC120123
0.8713	High Similarity	NPC211879
0.8713	High Similarity	NPC472252
0.8713	High Similarity	NPC213190
0.8713	High Similarity	NPC16520
0.8713	High Similarity	NPC473020
0.8713	High Similarity	NPC131479
0.8713	High Similarity	NPC157659
0.8713	High Similarity	NPC473198
0.8713	High Similarity	NPC245280
0.8713	High Similarity	NPC286969
0.8713	High Similarity	NPC189852
0.87	High Similarity	NPC155974
0.8687	High Similarity	NPC280825
0.8687	High Similarity	NPC234287
0.8687	High Similarity	NPC476895
0.8687	High Similarity	NPC477928
0.8679	High Similarity	NPC144068
0.8627	High Similarity	NPC470885
0.8627	High Similarity	NPC221562
0.8627	High Similarity	NPC85593
0.8627	High Similarity	NPC173583
0.8627	High Similarity	NPC273879
0.8627	High Similarity	NPC31430
0.8627	High Similarity	NPC187400
0.8627	High Similarity	NPC165033
0.8614	High Similarity	NPC159036
0.8614	High Similarity	NPC288694
0.8614	High Similarity	NPC312553
0.8614	High Similarity	NPC154452
0.86	High Similarity	NPC208358
0.8586	High Similarity	NPC476893
0.8558	High Similarity	NPC295980
0.8544	High Similarity	NPC152584
0.8544	High Similarity	NPC208594
0.8544	High Similarity	NPC269627
0.8544	High Similarity	NPC194842
0.8544	High Similarity	NPC160816
0.8544	High Similarity	NPC208477
0.8544	High Similarity	NPC470767
0.8544	High Similarity	NPC127801
0.8544	High Similarity	NPC165405
0.8544	High Similarity	NPC69737
0.8544	High Similarity	NPC470763
0.8529	High Similarity	NPC16573
0.8529	High Similarity	NPC474124
0.8519	High Similarity	NPC146652
0.8515	High Similarity	NPC121072
0.8515	High Similarity	NPC476896
0.8515	High Similarity	NPC476132
0.8515	High Similarity	NPC21064
0.8505	High Similarity	NPC255017
0.85	High Similarity	NPC157739
0.85	High Similarity	NPC477876
0.85	High Similarity	NPC477875
0.85	High Similarity	NPC102426
0.85	High Similarity	NPC300179
0.8491	Intermediate Similarity	NPC250481
0.8491	Intermediate Similarity	NPC263827
0.8491	Intermediate Similarity	NPC285410
0.8485	Intermediate Similarity	NPC472989
0.8485	Intermediate Similarity	NPC304899
0.8485	Intermediate Similarity	NPC471903
0.8485	Intermediate Similarity	NPC253115
0.8476	Intermediate Similarity	NPC477070
0.8476	Intermediate Similarity	NPC477069
0.8476	Intermediate Similarity	NPC472901
0.8469	Intermediate Similarity	NPC211238
0.8462	Intermediate Similarity	NPC14946
0.8462	Intermediate Similarity	NPC181467
0.8462	Intermediate Similarity	NPC208650
0.8462	Intermediate Similarity	NPC231340
0.8462	Intermediate Similarity	NPC63368
0.8462	Intermediate Similarity	NPC190395
0.8462	Intermediate Similarity	NPC473469
0.8455	Intermediate Similarity	NPC29639
0.8455	Intermediate Similarity	NPC5883
0.8455	Intermediate Similarity	NPC44899
0.8455	Intermediate Similarity	NPC304260
0.8447	Intermediate Similarity	NPC75608
0.8447	Intermediate Similarity	NPC470768
0.8447	Intermediate Similarity	NPC473543
0.844	Intermediate Similarity	NPC93883
0.8431	Intermediate Similarity	NPC476471
0.8431	Intermediate Similarity	NPC475344
0.8426	Intermediate Similarity	NPC472274
0.8426	Intermediate Similarity	NPC473882
0.8416	Intermediate Similarity	NPC317019
0.8416	Intermediate Similarity	NPC476195
0.8416	Intermediate Similarity	NPC282669
0.8416	Intermediate Similarity	NPC473790
0.8411	Intermediate Similarity	NPC46388
0.8411	Intermediate Similarity	NPC37739
0.84	Intermediate Similarity	NPC278939
0.84	Intermediate Similarity	NPC475032
0.84	Intermediate Similarity	NPC473890
0.84	Intermediate Similarity	NPC243728
0.84	Intermediate Similarity	NPC475033
0.84	Intermediate Similarity	NPC473555
0.84	Intermediate Similarity	NPC471770
0.8396	Intermediate Similarity	NPC52241
0.8396	Intermediate Similarity	NPC274507
0.8396	Intermediate Similarity	NPC475317
0.8396	Intermediate Similarity	NPC129340
0.8396	Intermediate Similarity	NPC154856
0.8381	Intermediate Similarity	NPC6931
0.8381	Intermediate Similarity	NPC7213
0.8381	Intermediate Similarity	NPC472897
0.8381	Intermediate Similarity	NPC472896
0.8381	Intermediate Similarity	NPC258323
0.8381	Intermediate Similarity	NPC180183
0.8381	Intermediate Similarity	NPC295389
0.8381	Intermediate Similarity	NPC220427
0.8381	Intermediate Similarity	NPC246124
0.8381	Intermediate Similarity	NPC159005
0.8365	Intermediate Similarity	NPC309448
0.8365	Intermediate Similarity	NPC242748
0.8365	Intermediate Similarity	NPC472655
0.8364	Intermediate Similarity	NPC472080
0.835	Intermediate Similarity	NPC475701
0.835	Intermediate Similarity	NPC473523
0.835	Intermediate Similarity	NPC471467
0.8349	Intermediate Similarity	NPC193382
0.8349	Intermediate Similarity	NPC199428
0.8349	Intermediate Similarity	NPC310341
0.8349	Intermediate Similarity	NPC99620
0.8349	Intermediate Similarity	NPC5311
0.8349	Intermediate Similarity	NPC212660
0.8333	Intermediate Similarity	NPC138334
0.8333	Intermediate Similarity	NPC269315
0.8333	Intermediate Similarity	NPC271138
0.8333	Intermediate Similarity	NPC189884
0.8333	Intermediate Similarity	NPC204458
0.8333	Intermediate Similarity	NPC251309
0.8333	Intermediate Similarity	NPC47063
0.8333	Intermediate Similarity	NPC289670
0.8333	Intermediate Similarity	NPC475617
0.8318	Intermediate Similarity	NPC30397
0.8318	Intermediate Similarity	NPC473021
0.8318	Intermediate Similarity	NPC108748
0.8318	Intermediate Similarity	NPC472987
0.8318	Intermediate Similarity	NPC190837
0.8318	Intermediate Similarity	NPC470748
0.8318	Intermediate Similarity	NPC473481
0.8318	Intermediate Similarity	NPC191763
0.8318	Intermediate Similarity	NPC211798
0.8318	Intermediate Similarity	NPC235841
0.8318	Intermediate Similarity	NPC297208
0.8318	Intermediate Similarity	NPC477073
0.8317	Intermediate Similarity	NPC158088
0.8304	Intermediate Similarity	NPC475219
0.8304	Intermediate Similarity	NPC231518
0.8302	Intermediate Similarity	NPC167383
0.8302	Intermediate Similarity	NPC204407
0.8302	Intermediate Similarity	NPC137917
0.8302	Intermediate Similarity	NPC265655

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 NPC470053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1945
0.2-0.3	3972
0.3-0.4	1993
0.4-0.5	611
0.5-0.6	283
0.6-0.7	120
0.7-0.8	31
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
0.8304	Intermediate Similarity	NPD8033	Approved
0.8214	Intermediate Similarity	NPD8377	Approved
0.8214	Intermediate Similarity	NPD8294	Approved
0.8198	Intermediate Similarity	NPD7328	Approved
0.8198	Intermediate Similarity	NPD7327	Approved
0.8142	Intermediate Similarity	NPD8378	Approved
0.8142	Intermediate Similarity	NPD8380	Approved
0.8142	Intermediate Similarity	NPD8296	Approved
0.8142	Intermediate Similarity	NPD8379	Approved
0.8142	Intermediate Similarity	NPD8335	Approved
0.8125	Intermediate Similarity	NPD7516	Approved
0.7798	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7507	Approved
0.7679	Intermediate Similarity	NPD8133	Approved
0.7672	Intermediate Similarity	NPD7503	Approved
0.7632	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7455	Intermediate Similarity	NPD6412	Phase 2
0.7453	Intermediate Similarity	NPD7638	Approved
0.7395	Intermediate Similarity	NPD8328	Phase 3
0.7387	Intermediate Similarity	NPD6686	Approved
0.7383	Intermediate Similarity	NPD7640	Approved
0.7383	Intermediate Similarity	NPD7639	Approved
0.7295	Intermediate Similarity	NPD7736	Approved
0.7281	Intermediate Similarity	NPD8297	Approved
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7157	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD8171	Discontinued
0.713	Intermediate Similarity	NPD6882	Approved
0.7075	Intermediate Similarity	NPD7748	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7069	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD7128	Approved
0.7054	Intermediate Similarity	NPD5739	Approved
0.7054	Intermediate Similarity	NPD6675	Approved
0.7054	Intermediate Similarity	NPD6402	Approved
0.7049	Intermediate Similarity	NPD7492	Approved
0.7041	Intermediate Similarity	NPD7645	Phase 2
0.7037	Intermediate Similarity	NPD7902	Approved
0.7034	Intermediate Similarity	NPD6009	Approved
0.7034	Intermediate Similarity	NPD7115	Discovery
0.703	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6373	Approved
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.6972	Remote Similarity	NPD4225	Approved
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7632	Discontinued
0.6935	Remote Similarity	NPD7078	Approved
0.6931	Remote Similarity	NPD6695	Phase 3
0.693	Remote Similarity	NPD7320	Approved
0.693	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6881	Approved
0.693	Remote Similarity	NPD6899	Approved
0.6897	Remote Similarity	NPD6649	Approved
0.6897	Remote Similarity	NPD6650	Approved
0.6897	Remote Similarity	NPD8130	Phase 1
0.6887	Remote Similarity	NPD7515	Phase 2
0.6885	Remote Similarity	NPD6370	Approved
0.6847	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD5701	Approved
0.6842	Remote Similarity	NPD5697	Approved
0.6827	Remote Similarity	NPD7750	Discontinued
0.6814	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6883	Approved
0.681	Remote Similarity	NPD7290	Approved
0.681	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7102	Approved
0.6804	Remote Similarity	NPD7339	Approved
0.6804	Remote Similarity	NPD6942	Approved
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.6803	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD6928	Phase 2
0.6759	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7900	Approved
0.6754	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6617	Approved
0.6752	Remote Similarity	NPD6869	Approved
0.6752	Remote Similarity	NPD6847	Approved
0.6752	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5988	Approved
0.6735	Remote Similarity	NPD6933	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6727	Remote Similarity	NPD6084	Phase 2
0.6727	Remote Similarity	NPD6083	Phase 2
0.6724	Remote Similarity	NPD6014	Approved
0.6724	Remote Similarity	NPD6013	Approved
0.6724	Remote Similarity	NPD6012	Approved
0.6699	Remote Similarity	NPD4786	Approved
0.6694	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD6011	Approved
0.6634	Remote Similarity	NPD6930	Phase 2
0.6634	Remote Similarity	NPD6931	Approved
0.6634	Remote Similarity	NPD7509	Discontinued
0.6632	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6114	Approved
0.66	Remote Similarity	NPD6115	Approved
0.66	Remote Similarity	NPD6118	Approved
0.66	Remote Similarity	NPD6697	Approved
0.6587	Remote Similarity	NPD6336	Discontinued
0.6577	Remote Similarity	NPD4755	Approved
0.6566	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6051	Approved
0.6542	Remote Similarity	NPD5328	Approved
0.6538	Remote Similarity	NPD8449	Approved
0.6535	Remote Similarity	NPD6929	Approved
0.6531	Remote Similarity	NPD6924	Approved
0.6531	Remote Similarity	NPD6926	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD7625	Phase 1
0.6518	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4202	Approved
0.6509	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3667	Approved
0.65	Remote Similarity	NPD6116	Phase 1
0.65	Remote Similarity	NPD6932	Approved
0.6489	Remote Similarity	NPD8450	Suspended
0.6484	Remote Similarity	NPD6033	Approved
0.6481	Remote Similarity	NPD7838	Discovery
0.6481	Remote Similarity	NPD6698	Approved
0.6481	Remote Similarity	NPD46	Approved
0.6481	Remote Similarity	NPD3168	Discontinued
0.6471	Remote Similarity	NPD7332	Phase 2
0.646	Remote Similarity	NPD4696	Approved
0.646	Remote Similarity	NPD6648	Approved
0.646	Remote Similarity	NPD5285	Approved
0.646	Remote Similarity	NPD4700	Approved
0.646	Remote Similarity	NPD5286	Approved
0.6449	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6067	Discontinued
0.6422	Remote Similarity	NPD7087	Discontinued
0.6422	Remote Similarity	NPD6079	Approved
0.6422	Remote Similarity	NPD6411	Approved
0.6415	Remote Similarity	NPD3618	Phase 1
0.6408	Remote Similarity	NPD6898	Phase 1
0.6406	Remote Similarity	NPD8074	Phase 3
0.64	Remote Similarity	NPD6921	Approved
0.64	Remote Similarity	NPD6117	Approved
0.6396	Remote Similarity	NPD5695	Phase 3
0.6393	Remote Similarity	NPD6274	Approved
0.6373	Remote Similarity	NPD6683	Phase 2
0.6372	Remote Similarity	NPD5696	Approved
0.6371	Remote Similarity	NPD7100	Approved
0.6371	Remote Similarity	NPD7101	Approved
0.6348	Remote Similarity	NPD4633	Approved
0.6348	Remote Similarity	NPD5224	Approved
0.6348	Remote Similarity	NPD5211	Phase 2
0.6348	Remote Similarity	NPD5225	Approved
0.6348	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD6925	Approved
0.6337	Remote Similarity	NPD5776	Phase 2
0.6325	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD4768	Approved
0.6321	Remote Similarity	NPD6893	Approved
0.6311	Remote Similarity	NPD4748	Discontinued
0.6311	Remote Similarity	NPD7514	Phase 3
0.6296	Remote Similarity	NPD6672	Approved
0.6296	Remote Similarity	NPD5737	Approved
0.6293	Remote Similarity	NPD5174	Approved
0.6293	Remote Similarity	NPD5175	Approved
0.629	Remote Similarity	NPD6335	Approved
0.6286	Remote Similarity	NPD3669	Approved
0.6286	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6053	Discontinued
0.6275	Remote Similarity	NPD7145	Approved
0.6273	Remote Similarity	NPD7983	Approved
0.6271	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6909	Approved
0.627	Remote Similarity	NPD6908	Approved
0.6262	Remote Similarity	NPD7146	Approved
0.6262	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6684	Approved
0.6262	Remote Similarity	NPD5330	Approved
0.6262	Remote Similarity	NPD7521	Approved
0.6262	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD5223	Approved
0.6261	Remote Similarity	NPD4159	Approved
0.626	Remote Similarity	NPD6940	Discontinued
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD5141	Approved
0.6239	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6101	Approved
0.6239	Remote Similarity	NPD4753	Phase 2
0.6224	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4730	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