NPASS Compound

Structure

CID297617 OpenBabel06191716102D 35 40 0 0 1 0 0 0 0 0999 V2000 5.5554 1.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9885 -2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 -0.3572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0917 -1.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9156 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 0.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2464 0.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3194 -1.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6284 -1.0102 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5283 1.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2683 0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7969 -0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0283 2.5132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5991 1.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 -0.2670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0917 0.8209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 23 1 0 0 0 0 11 28 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 29 1 0 0 0 0 16 30 1 0 0 0 0 17 25 1 0 0 0 0 18 2 1 1 0 0 0 18 19 1 0 0 0 0 19 27 1 1 0 0 0 20 24 1 0 0 0 0 20 31 1 1 0 0 0 21 18 1 1 0 0 0 21 34 1 0 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 32 2 0 0 0 0 23 35 1 0 0 0 0 24 26 1 0 0 0 0 24 30 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 12 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.3
Volume:	509.503
LogP:	5.858
LogD:	4.282
LogS:	-4.803
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	6.116
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.068
MDCK Permeability:	2.3842654627515003e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	93.11497497558594%
Volume Distribution (VD):	1.701
Pgp-substrate:	6.263338088989258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.257
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.629
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.778
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.752

ADMET: Excretion

Clearance (CL):	9.181
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.745
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.961
Carcinogencity:	0.78
Eye Corrosion:	0.054
Eye Irritation:	0.035
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC297617

Natural Product ID:	NPC297617
*Common Name:**	Kadsulactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	APOPUTYAPYVYFW-HLNDSBHSSA-N
Standard InCHI:	InChI=1S/C30H42O5/c1-17-7-8-21(34-25(17)33)18(2)19-9-11-28(6)22-15-20(31)24-26(3,4)35-23(32)10-12-30(24)16-29(22,30)14-13-27(19,28)5/h7,10,12,18-22,24,31H,8-9,11,13-16H2,1-6H3/t18-,19+,20+,21-,22-,24-,27+,28-,29-,30+/m0/s1
SMILES:	CC1=CC[C@@H]([C@@H](C)[C@H]2CC[C@@]3(C)[C@@H]4C[C@H]([C@H]5C(C)(C)OC(=O)C=C[C@]65C[C@@]46CC[C@]23C)O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455083
PubChem CID:	153922
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
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16557460]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	8.6	ug.mL-1	PMID[451658]

☑ 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 NPC297617 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	192
0.1-0.2	1201
0.2-0.3	4298
0.3-0.4	11182
0.4-0.5	10907
0.5-0.6	7032
0.6-0.7	5704
0.7-0.8	2025
0.8-0.85	134
0.85-0.9	18
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9314	High Similarity	NPC470076
0.8962	High Similarity	NPC470075
0.8788	High Similarity	NPC98868
0.8763	High Similarity	NPC476186
0.87	High Similarity	NPC227865
0.866	High Similarity	NPC476304
0.8627	High Similarity	NPC112009
0.86	High Similarity	NPC218107
0.8598	High Similarity	NPC122056
0.8586	High Similarity	NPC114743
0.8586	High Similarity	NPC195366
0.8571	High Similarity	NPC201725
0.8571	High Similarity	NPC75389
0.8558	High Similarity	NPC79298
0.8558	High Similarity	NPC43063
0.8557	High Similarity	NPC74296
0.8557	High Similarity	NPC110923
0.8485	Intermediate Similarity	NPC33473
0.8476	Intermediate Similarity	NPC275060
0.8469	Intermediate Similarity	NPC38232
0.8469	Intermediate Similarity	NPC205034
0.8469	Intermediate Similarity	NPC152778
0.8469	Intermediate Similarity	NPC162615
0.8462	Intermediate Similarity	NPC266570
0.8454	Intermediate Similarity	NPC78973
0.8447	Intermediate Similarity	NPC476237
0.8447	Intermediate Similarity	NPC180204
0.8447	Intermediate Similarity	NPC171014
0.8411	Intermediate Similarity	NPC284162
0.8411	Intermediate Similarity	NPC255401
0.84	Intermediate Similarity	NPC16967
0.8384	Intermediate Similarity	NPC119562
0.8384	Intermediate Similarity	NPC279410
0.8367	Intermediate Similarity	NPC177641
0.8367	Intermediate Similarity	NPC72845
0.8365	Intermediate Similarity	NPC272632
0.8364	Intermediate Similarity	NPC167606
0.8364	Intermediate Similarity	NPC286528
0.8364	Intermediate Similarity	NPC20302
0.8364	Intermediate Similarity	NPC140055
0.8351	Intermediate Similarity	NPC177141
0.8351	Intermediate Similarity	NPC146554
0.8351	Intermediate Similarity	NPC262858
0.8351	Intermediate Similarity	NPC472240
0.835	Intermediate Similarity	NPC32577
0.835	Intermediate Similarity	NPC114540
0.835	Intermediate Similarity	NPC155332
0.8349	Intermediate Similarity	NPC147912
0.8349	Intermediate Similarity	NPC216665
0.8349	Intermediate Similarity	NPC67259
0.8333	Intermediate Similarity	NPC473510
0.8333	Intermediate Similarity	NPC201406
0.8333	Intermediate Similarity	NPC476303
0.8333	Intermediate Similarity	NPC44537
0.8318	Intermediate Similarity	NPC238850
0.8318	Intermediate Similarity	NPC103491
0.8317	Intermediate Similarity	NPC210337
0.8317	Intermediate Similarity	NPC99726
0.8317	Intermediate Similarity	NPC141401
0.8302	Intermediate Similarity	NPC304276
0.8302	Intermediate Similarity	NPC137462
0.83	Intermediate Similarity	NPC276110
0.8288	Intermediate Similarity	NPC50774
0.8288	Intermediate Similarity	NPC709
0.8286	Intermediate Similarity	NPC220217
0.8286	Intermediate Similarity	NPC295843
0.8286	Intermediate Similarity	NPC119855
0.8269	Intermediate Similarity	NPC189588
0.8269	Intermediate Similarity	NPC97487
0.8269	Intermediate Similarity	NPC10232
0.8269	Intermediate Similarity	NPC196471
0.8269	Intermediate Similarity	NPC183570
0.8269	Intermediate Similarity	NPC176883
0.8269	Intermediate Similarity	NPC187302
0.8265	Intermediate Similarity	NPC273199
0.8265	Intermediate Similarity	NPC302280
0.8265	Intermediate Similarity	NPC310479
0.8257	Intermediate Similarity	NPC171126
0.8252	Intermediate Similarity	NPC268829
0.8252	Intermediate Similarity	NPC222875
0.8252	Intermediate Similarity	NPC247701
0.8252	Intermediate Similarity	NPC295110
0.8252	Intermediate Similarity	NPC25177
0.8241	Intermediate Similarity	NPC471484
0.8241	Intermediate Similarity	NPC262083
0.8241	Intermediate Similarity	NPC474315
0.8235	Intermediate Similarity	NPC108368
0.8235	Intermediate Similarity	NPC57079
0.8235	Intermediate Similarity	NPC92275
0.8229	Intermediate Similarity	NPC474970
0.8229	Intermediate Similarity	NPC131813
0.8218	Intermediate Similarity	NPC54248
0.8218	Intermediate Similarity	NPC276103
0.8218	Intermediate Similarity	NPC190713
0.8218	Intermediate Similarity	NPC162346
0.8218	Intermediate Similarity	NPC88009
0.8214	Intermediate Similarity	NPC264954
0.8208	Intermediate Similarity	NPC475294
0.82	Intermediate Similarity	NPC166143
0.82	Intermediate Similarity	NPC471994
0.82	Intermediate Similarity	NPC120351
0.82	Intermediate Similarity	NPC191521
0.8198	Intermediate Similarity	NPC470492
0.8198	Intermediate Similarity	NPC185287
0.8198	Intermediate Similarity	NPC243065
0.8198	Intermediate Similarity	NPC470493
0.8198	Intermediate Similarity	NPC183580
0.8198	Intermediate Similarity	NPC157380
0.8198	Intermediate Similarity	NPC312824
0.8182	Intermediate Similarity	NPC43213
0.8182	Intermediate Similarity	NPC234335
0.8173	Intermediate Similarity	NPC475038
0.8173	Intermediate Similarity	NPC109195
0.8165	Intermediate Similarity	NPC69291
0.8155	Intermediate Similarity	NPC474012
0.8155	Intermediate Similarity	NPC290802
0.8155	Intermediate Similarity	NPC476299
0.8155	Intermediate Similarity	NPC230546
0.8155	Intermediate Similarity	NPC251680
0.8148	Intermediate Similarity	NPC16270
0.8148	Intermediate Similarity	NPC12795
0.8144	Intermediate Similarity	NPC166857
0.8144	Intermediate Similarity	NPC149224
0.8142	Intermediate Similarity	NPC474370
0.8137	Intermediate Similarity	NPC253826
0.8137	Intermediate Similarity	NPC202705
0.8137	Intermediate Similarity	NPC231751
0.8137	Intermediate Similarity	NPC73911
0.8125	Intermediate Similarity	NPC16701
0.8119	Intermediate Similarity	NPC281134
0.8119	Intermediate Similarity	NPC293052
0.8113	Intermediate Similarity	NPC189863
0.81	Intermediate Similarity	NPC139692
0.81	Intermediate Similarity	NPC214697
0.8095	Intermediate Similarity	NPC280566
0.8095	Intermediate Similarity	NPC160583
0.8091	Intermediate Similarity	NPC241977
0.8081	Intermediate Similarity	NPC280149
0.8081	Intermediate Similarity	NPC182136
0.8081	Intermediate Similarity	NPC221111
0.8077	Intermediate Similarity	NPC115899
0.8077	Intermediate Similarity	NPC475617
0.807	Intermediate Similarity	NPC67569
0.8061	Intermediate Similarity	NPC93411
0.8058	Intermediate Similarity	NPC474440
0.8058	Intermediate Similarity	NPC252295
0.8056	Intermediate Similarity	NPC472216
0.8056	Intermediate Similarity	NPC475065
0.8056	Intermediate Similarity	NPC284828
0.8056	Intermediate Similarity	NPC173905
0.8056	Intermediate Similarity	NPC5475
0.8053	Intermediate Similarity	NPC213761
0.8053	Intermediate Similarity	NPC35171
0.8053	Intermediate Similarity	NPC278681
0.8039	Intermediate Similarity	NPC307164
0.8039	Intermediate Similarity	NPC473153
0.8037	Intermediate Similarity	NPC329048
0.8037	Intermediate Similarity	NPC330011
0.8037	Intermediate Similarity	NPC91034
0.8037	Intermediate Similarity	NPC263729
0.8036	Intermediate Similarity	NPC476959
0.8021	Intermediate Similarity	NPC470077
0.802	Intermediate Similarity	NPC105490
0.802	Intermediate Similarity	NPC469697
0.802	Intermediate Similarity	NPC57117
0.8019	Intermediate Similarity	NPC165969
0.8019	Intermediate Similarity	NPC473543
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC470063
0.8	Intermediate Similarity	NPC153700
0.8	Intermediate Similarity	NPC277769
0.8	Intermediate Similarity	NPC475344
0.8	Intermediate Similarity	NPC100267
0.8	Intermediate Similarity	NPC273668
0.8	Intermediate Similarity	NPC470265
0.8	Intermediate Similarity	NPC88326
0.8	Intermediate Similarity	NPC476471
0.8	Intermediate Similarity	NPC4573
0.8	Intermediate Similarity	NPC475524
0.8	Intermediate Similarity	NPC23786
0.8	Intermediate Similarity	NPC212948
0.8	Intermediate Similarity	NPC329842
0.7982	Intermediate Similarity	NPC112936
0.7981	Intermediate Similarity	NPC38855
0.7981	Intermediate Similarity	NPC470906
0.7981	Intermediate Similarity	NPC266955
0.7981	Intermediate Similarity	NPC470074
0.798	Intermediate Similarity	NPC473647
0.798	Intermediate Similarity	NPC50488
0.798	Intermediate Similarity	NPC128496
0.798	Intermediate Similarity	NPC82876
0.798	Intermediate Similarity	NPC474396
0.7965	Intermediate Similarity	NPC311554
0.7965	Intermediate Similarity	NPC257457
0.7963	Intermediate Similarity	NPC318363
0.7963	Intermediate Similarity	NPC472825
0.7963	Intermediate Similarity	NPC473482
0.7963	Intermediate Similarity	NPC475418
0.7963	Intermediate Similarity	NPC220155
0.7961	Intermediate Similarity	NPC110937

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 NPC297617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1333
0.2-0.3	3825
0.3-0.4	2632
0.4-0.5	740
0.5-0.6	184
0.6-0.7	202
0.7-0.8	75
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8364	Intermediate Similarity	NPD7115	Discovery
0.8235	Intermediate Similarity	NPD7638	Approved
0.8155	Intermediate Similarity	NPD7639	Approved
0.8155	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD4225	Approved
0.7798	Intermediate Similarity	NPD6881	Approved
0.7798	Intermediate Similarity	NPD6899	Approved
0.7706	Intermediate Similarity	NPD5697	Approved
0.7658	Intermediate Similarity	NPD6883	Approved
0.7658	Intermediate Similarity	NPD7290	Approved
0.7658	Intermediate Similarity	NPD7102	Approved
0.7615	Intermediate Similarity	NPD6675	Approved
0.7615	Intermediate Similarity	NPD6402	Approved
0.7615	Intermediate Similarity	NPD7128	Approved
0.7615	Intermediate Similarity	NPD5739	Approved
0.7589	Intermediate Similarity	NPD6617	Approved
0.7589	Intermediate Similarity	NPD6847	Approved
0.7589	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD8130	Phase 1
0.7589	Intermediate Similarity	NPD6869	Approved
0.7589	Intermediate Similarity	NPD6649	Approved
0.7568	Intermediate Similarity	NPD6013	Approved
0.7568	Intermediate Similarity	NPD6012	Approved
0.7568	Intermediate Similarity	NPD6014	Approved
0.7522	Intermediate Similarity	NPD6882	Approved
0.7522	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD7632	Discontinued
0.7477	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7476	Intermediate Similarity	NPD6079	Approved
0.7458	Intermediate Similarity	NPD7503	Approved
0.7453	Intermediate Similarity	NPD6083	Phase 2
0.7453	Intermediate Similarity	NPD6084	Phase 2
0.7451	Intermediate Similarity	NPD6051	Approved
0.7423	Intermediate Similarity	NPD7525	Registered
0.7411	Intermediate Similarity	NPD6373	Approved
0.7411	Intermediate Similarity	NPD6372	Approved
0.7404	Intermediate Similarity	NPD6399	Phase 3
0.7387	Intermediate Similarity	NPD5701	Approved
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7339	Intermediate Similarity	NPD5211	Phase 2
0.7315	Intermediate Similarity	NPD5286	Approved
0.7315	Intermediate Similarity	NPD4696	Approved
0.7315	Intermediate Similarity	NPD5285	Approved
0.7311	Intermediate Similarity	NPD8033	Approved
0.7308	Intermediate Similarity	NPD7637	Suspended
0.7288	Intermediate Similarity	NPD7516	Approved
0.7282	Intermediate Similarity	NPD5328	Approved
0.7264	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7227	Intermediate Similarity	NPD8294	Approved
0.7227	Intermediate Similarity	NPD8377	Approved
0.7217	Intermediate Similarity	NPD6053	Discontinued
0.7207	Intermediate Similarity	NPD5141	Approved
0.7196	Intermediate Similarity	NPD5221	Approved
0.7196	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5222	Approved
0.7182	Intermediate Similarity	NPD5226	Approved
0.7182	Intermediate Similarity	NPD4633	Approved
0.7182	Intermediate Similarity	NPD5225	Approved
0.7182	Intermediate Similarity	NPD5224	Approved
0.717	Intermediate Similarity	NPD7748	Approved
0.7167	Intermediate Similarity	NPD8296	Approved
0.7167	Intermediate Similarity	NPD8380	Approved
0.7167	Intermediate Similarity	NPD8335	Approved
0.7167	Intermediate Similarity	NPD8379	Approved
0.7167	Intermediate Similarity	NPD8378	Approved
0.7157	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD4755	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5173	Approved
0.7129	Intermediate Similarity	NPD4786	Approved
0.7117	Intermediate Similarity	NPD5174	Approved
0.7117	Intermediate Similarity	NPD5175	Approved
0.7105	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5695	Phase 3
0.71	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5223	Approved
0.7083	Intermediate Similarity	NPD7339	Approved
0.7083	Intermediate Similarity	NPD6942	Approved
0.7075	Intermediate Similarity	NPD4202	Approved
0.7073	Intermediate Similarity	NPD7507	Approved
0.7064	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6335	Approved
0.7049	Intermediate Similarity	NPD7604	Phase 2
0.7034	Intermediate Similarity	NPD6868	Approved
0.7034	Intermediate Similarity	NPD6274	Approved
0.703	Intermediate Similarity	NPD6695	Phase 3
0.7019	Intermediate Similarity	NPD5737	Approved
0.7019	Intermediate Similarity	NPD6672	Approved
0.7018	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.7	Intermediate Similarity	NPD4700	Approved
0.6991	Remote Similarity	NPD6008	Approved
0.699	Remote Similarity	NPD5330	Approved
0.699	Remote Similarity	NPD7146	Approved
0.699	Remote Similarity	NPD7521	Approved
0.699	Remote Similarity	NPD6409	Approved
0.699	Remote Similarity	NPD6684	Approved
0.699	Remote Similarity	NPD7334	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6981	Remote Similarity	NPD8035	Phase 2
0.6981	Remote Similarity	NPD8034	Phase 2
0.6975	Remote Similarity	NPD6317	Approved
0.6972	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD4195	Approved
0.6961	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4753	Phase 2
0.6944	Remote Similarity	NPD5210	Approved
0.6944	Remote Similarity	NPD4629	Approved
0.6942	Remote Similarity	NPD6319	Approved
0.6931	Remote Similarity	NPD3667	Approved
0.6917	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD6314	Approved
0.6905	Remote Similarity	NPD7319	Approved
0.6897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1694	Approved
0.6887	Remote Similarity	NPD5785	Approved
0.6881	Remote Similarity	NPD4697	Phase 3
0.687	Remote Similarity	NPD4730	Approved
0.687	Remote Similarity	NPD4729	Approved
0.6857	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6903	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6852	Remote Similarity	NPD6001	Approved
0.6837	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6009	Approved
0.6832	Remote Similarity	NPD6902	Approved
0.6804	Remote Similarity	NPD6926	Approved
0.6804	Remote Similarity	NPD6924	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD7645	Phase 2
0.68	Remote Similarity	NPD6616	Approved
0.6796	Remote Similarity	NPD3665	Phase 1
0.6796	Remote Similarity	NPD3133	Approved
0.6796	Remote Similarity	NPD3666	Approved
0.6792	Remote Similarity	NPD6080	Approved
0.6792	Remote Similarity	NPD6673	Approved
0.6792	Remote Similarity	NPD6904	Approved
0.6762	Remote Similarity	NPD7750	Discontinued
0.6762	Remote Similarity	NPD3573	Approved
0.6762	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7524	Approved
0.6752	Remote Similarity	NPD5249	Phase 3
0.6752	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD5247	Approved
0.6752	Remote Similarity	NPD6371	Approved
0.6752	Remote Similarity	NPD5250	Approved
0.6752	Remote Similarity	NPD5251	Approved
0.6752	Remote Similarity	NPD5248	Approved
0.6748	Remote Similarity	NPD5983	Phase 2
0.6748	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6908	Approved
0.6748	Remote Similarity	NPD6909	Approved
0.6746	Remote Similarity	NPD7078	Approved
0.6733	Remote Similarity	NPD6930	Phase 2
0.6733	Remote Similarity	NPD7514	Phase 3
0.6733	Remote Similarity	NPD6931	Approved
0.6729	Remote Similarity	NPD7838	Discovery
0.6724	Remote Similarity	NPD5128	Approved
0.6697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7900	Approved
0.6696	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6695	Remote Similarity	NPD5217	Approved
0.6695	Remote Similarity	NPD5215	Approved
0.6695	Remote Similarity	NPD5216	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5281	Approved
0.6638	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4159	Approved
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6929	Approved
0.6633	Remote Similarity	NPD4785	Approved
0.6633	Remote Similarity	NPD4784	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.6613	Remote Similarity	NPD6016	Approved
0.661	Remote Similarity	NPD5169	Approved
0.661	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5135	Approved
0.6607	Remote Similarity	NPD5290	Discontinued
0.6602	Remote Similarity	NPD4223	Phase 3
0.6602	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD6932	Approved
0.6598	Remote Similarity	NPD7150	Approved
0.6598	Remote Similarity	NPD7151	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