NPASS Compound

Structure

CID239118 OpenBabel06191716042D 31 35 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 3.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 1 13 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 6 9 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 29 1 0 0 0 0 13 26 2 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 21 2 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 1 0 0 0 19 24 1 1 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 20 30 1 1 0 0 0 21 31 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 6 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.22
Volume:	437.733
LogP:	5.308
LogD:	4.163
LogS:	-4.357
# Rotatable Bonds:	2
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.598
Synthetic Accessibility Score:	4.6
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.934
MDCK Permeability:	1.8485223336028866e-05
Pgp-inhibitor:	0.212
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	94.4600601196289%
Volume Distribution (VD):	1.147
Pgp-substrate:	10.478743553161621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.242
CYP2C9-substrate:	0.583
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	11.101
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.683
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.329
Carcinogencity:	0.154
Eye Corrosion:	0.003
Eye Irritation:	0.304
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC239118

Natural Product ID:	NPC239118
*Common Name:**	Kampanol A
IUPAC Name:	n.a.
Synonyms:	Kampanol A
Standard InCHIKey:	BOVRDZLKBBUXQQ-BOWIAGTOSA-N
Standard InCHI:	InChI=1S/C25H32O6/c1-13(26)30-20-7-8-24(4)18(23(20,2)3)6-9-25(5)19(24)11-15-17(27)10-14-16(21(15)31-25)12-29-22(14)28/h10,18-20,27H,6-9,11-12H2,1-5H3/t18-,19+,20-,24-,25-/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@]1([C@@H]2Cc2c(O)cc3c(c2O1)COC3=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL62448
PubChem CID:	10094096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001828] Isoflavanols

*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
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341709]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21341709]
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9873488]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18301	Stachybotrys kampalensis	Species	Stachybotryaceae	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	7

Activity Type	# Activity
NON-MOLECULAR	5
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	13000.0	nM	PMID[521739]
NPT2	Others	Unspecified		IC50	n.a.	100000.0	nM	PMID[521739]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[521740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19.6	ug.mL-1	PMID[521740]

☑ 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 NPC239118 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	363
0.1-0.2	1444
0.2-0.3	2942
0.3-0.4	6021
0.4-0.5	10717
0.5-0.6	6133
0.6-0.7	5603
0.7-0.8	8739
0.8-0.85	671
0.85-0.9	49
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC4950
0.9801	High Similarity	NPC158542
0.9608	High Similarity	NPC218818
0.9245	High Similarity	NPC125465
0.9	High Similarity	NPC100849
0.8981	High Similarity	NPC477674
0.8974	High Similarity	NPC477669
0.8968	High Similarity	NPC477673
0.8968	High Similarity	NPC477672
0.8947	High Similarity	NPC471608
0.8938	High Similarity	NPC473022
0.8917	High Similarity	NPC477687
0.8917	High Similarity	NPC477671
0.8889	High Similarity	NPC472621
0.8868	High Similarity	NPC226287
0.8868	High Similarity	NPC472617
0.8861	High Similarity	NPC477675
0.8854	High Similarity	NPC472799
0.8846	High Similarity	NPC476452
0.8834	High Similarity	NPC472622
0.8827	High Similarity	NPC316262
0.8827	High Similarity	NPC314653
0.8812	High Similarity	NPC472618
0.8805	High Similarity	NPC272196
0.8795	High Similarity	NPC294149
0.8788	High Similarity	NPC472620
0.8742	High Similarity	NPC4547
0.8727	High Similarity	NPC477571
0.8727	High Similarity	NPC477572
0.8727	High Similarity	NPC477573
0.8726	High Similarity	NPC48671
0.871	High Similarity	NPC66991
0.8696	High Similarity	NPC470810
0.8693	High Similarity	NPC3732
0.8688	High Similarity	NPC123153
0.8688	High Similarity	NPC196448
0.8671	High Similarity	NPC217447
0.8671	High Similarity	NPC271681
0.8667	High Similarity	NPC472619
0.8662	High Similarity	NPC477676
0.8662	High Similarity	NPC150928
0.8654	High Similarity	NPC146388
0.8647	High Similarity	NPC475148
0.8647	High Similarity	NPC475656
0.8645	High Similarity	NPC286038
0.8634	High Similarity	NPC186113
0.8634	High Similarity	NPC472299
0.8634	High Similarity	NPC474373
0.8631	High Similarity	NPC472661
0.8631	High Similarity	NPC324220
0.8631	High Similarity	NPC312630
0.8625	High Similarity	NPC146211
0.8614	High Similarity	NPC313717
0.8614	High Similarity	NPC315306
0.8608	High Similarity	NPC473131
0.8608	High Similarity	NPC478148
0.8608	High Similarity	NPC470675
0.8608	High Similarity	NPC149085
0.8606	High Similarity	NPC76647
0.8589	High Similarity	NPC473961
0.8589	High Similarity	NPC475106
0.858	High Similarity	NPC313368
0.8563	High Similarity	NPC118128
0.8553	High Similarity	NPC87708
0.8553	High Similarity	NPC273483
0.8553	High Similarity	NPC477690
0.8553	High Similarity	NPC40356
0.8553	High Similarity	NPC154683
0.8553	High Similarity	NPC44606
0.8545	High Similarity	NPC291742
0.8545	High Similarity	NPC255787
0.8544	High Similarity	NPC225854
0.8544	High Similarity	NPC119929
0.8544	High Similarity	NPC13282
0.8537	High Similarity	NPC308156
0.8521	High Similarity	NPC478050
0.8521	High Similarity	NPC475233
0.8519	High Similarity	NPC470339
0.8519	High Similarity	NPC477692
0.8516	High Similarity	NPC295696
0.8516	High Similarity	NPC71739
0.8503	High Similarity	NPC313304
0.8503	High Similarity	NPC241874
0.85	High Similarity	NPC135522
0.85	High Similarity	NPC477691
0.8491	Intermediate Similarity	NPC72958
0.8491	Intermediate Similarity	NPC305965
0.8491	Intermediate Similarity	NPC149526
0.8491	Intermediate Similarity	NPC474417
0.8491	Intermediate Similarity	NPC232645
0.8491	Intermediate Similarity	NPC39819
0.8481	Intermediate Similarity	NPC291049
0.8481	Intermediate Similarity	NPC233267
0.8481	Intermediate Similarity	NPC70764
0.8481	Intermediate Similarity	NPC146014
0.848	Intermediate Similarity	NPC208069
0.8476	Intermediate Similarity	NPC472402
0.8476	Intermediate Similarity	NPC15374
0.8476	Intermediate Similarity	NPC477528
0.8471	Intermediate Similarity	NPC77903
0.8471	Intermediate Similarity	NPC137296
0.8471	Intermediate Similarity	NPC142863
0.8471	Intermediate Similarity	NPC8817
0.8471	Intermediate Similarity	NPC17101
0.8466	Intermediate Similarity	NPC472055
0.8462	Intermediate Similarity	NPC117716
0.8462	Intermediate Similarity	NPC75694
0.8462	Intermediate Similarity	NPC470673
0.8462	Intermediate Similarity	NPC470674
0.8462	Intermediate Similarity	NPC68381
0.8443	Intermediate Similarity	NPC291795
0.8443	Intermediate Similarity	NPC207574
0.8443	Intermediate Similarity	NPC297195
0.8443	Intermediate Similarity	NPC102810
0.8438	Intermediate Similarity	NPC180944
0.8434	Intermediate Similarity	NPC477835
0.8434	Intermediate Similarity	NPC472452
0.8428	Intermediate Similarity	NPC179178
0.8428	Intermediate Similarity	NPC140133
0.8428	Intermediate Similarity	NPC470568
0.8428	Intermediate Similarity	NPC202595
0.8428	Intermediate Similarity	NPC158866
0.8424	Intermediate Similarity	NPC473009
0.8421	Intermediate Similarity	NPC473729
0.8418	Intermediate Similarity	NPC105415
0.8418	Intermediate Similarity	NPC95526
0.8418	Intermediate Similarity	NPC37139
0.8415	Intermediate Similarity	NPC18380
0.8415	Intermediate Similarity	NPC117985
0.8415	Intermediate Similarity	NPC92589
0.8415	Intermediate Similarity	NPC137232
0.8408	Intermediate Similarity	NPC470676
0.8408	Intermediate Similarity	NPC469758
0.8408	Intermediate Similarity	NPC470357
0.8408	Intermediate Similarity	NPC473135
0.8408	Intermediate Similarity	NPC473132
0.8402	Intermediate Similarity	NPC98776
0.8402	Intermediate Similarity	NPC476311
0.8402	Intermediate Similarity	NPC475080
0.8397	Intermediate Similarity	NPC471451
0.8397	Intermediate Similarity	NPC260152
0.8395	Intermediate Similarity	NPC55463
0.8395	Intermediate Similarity	NPC166116
0.8395	Intermediate Similarity	NPC180924
0.8393	Intermediate Similarity	NPC298778
0.8393	Intermediate Similarity	NPC241387
0.8393	Intermediate Similarity	NPC180768
0.8393	Intermediate Similarity	NPC193698
0.8393	Intermediate Similarity	NPC251144
0.8393	Intermediate Similarity	NPC477670
0.8385	Intermediate Similarity	NPC60084
0.8385	Intermediate Similarity	NPC169990
0.8385	Intermediate Similarity	NPC329844
0.8385	Intermediate Similarity	NPC210942
0.8383	Intermediate Similarity	NPC472660
0.8383	Intermediate Similarity	NPC225419
0.8377	Intermediate Similarity	NPC155552
0.8375	Intermediate Similarity	NPC148945
0.8375	Intermediate Similarity	NPC78835
0.8375	Intermediate Similarity	NPC309512
0.8375	Intermediate Similarity	NPC316960
0.8375	Intermediate Similarity	NPC133856
0.8375	Intermediate Similarity	NPC317715
0.8375	Intermediate Similarity	NPC204561
0.8375	Intermediate Similarity	NPC470569
0.8373	Intermediate Similarity	NPC473010
0.8373	Intermediate Similarity	NPC473286
0.8372	Intermediate Similarity	NPC475161
0.8372	Intermediate Similarity	NPC477860
0.8365	Intermediate Similarity	NPC212257
0.8365	Intermediate Similarity	NPC471114
0.8365	Intermediate Similarity	NPC103116
0.8364	Intermediate Similarity	NPC473012
0.8354	Intermediate Similarity	NPC184326
0.8354	Intermediate Similarity	NPC292863
0.8354	Intermediate Similarity	NPC150215
0.8354	Intermediate Similarity	NPC71055
0.8354	Intermediate Similarity	NPC143050
0.8354	Intermediate Similarity	NPC125801
0.8353	Intermediate Similarity	NPC474345
0.8344	Intermediate Similarity	NPC143328
0.8344	Intermediate Similarity	NPC469764
0.8344	Intermediate Similarity	NPC263483
0.8344	Intermediate Similarity	NPC246647
0.8344	Intermediate Similarity	NPC44199
0.8344	Intermediate Similarity	NPC281137
0.8344	Intermediate Similarity	NPC96342
0.8344	Intermediate Similarity	NPC212967
0.8344	Intermediate Similarity	NPC474611
0.8344	Intermediate Similarity	NPC282390
0.8344	Intermediate Similarity	NPC164110
0.8344	Intermediate Similarity	NPC131766
0.8343	Intermediate Similarity	NPC271385
0.8343	Intermediate Similarity	NPC30432
0.8343	Intermediate Similarity	NPC76128
0.8343	Intermediate Similarity	NPC5029
0.8343	Intermediate Similarity	NPC477836
0.8343	Intermediate Similarity	NPC111536
0.8333	Intermediate Similarity	NPC471731
0.8333	Intermediate Similarity	NPC159721

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 NPC239118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	919
0.2-0.3	1651
0.3-0.4	2480
0.4-0.5	2041
0.5-0.6	1100
0.6-0.7	459
0.7-0.8	174
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD6398	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2533	Approved
0.8462	Intermediate Similarity	NPD2534	Approved
0.8462	Intermediate Similarity	NPD2532	Approved
0.8443	Intermediate Similarity	NPD5844	Phase 1
0.8415	Intermediate Similarity	NPD6959	Discontinued
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8282	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD6099	Approved
0.8182	Intermediate Similarity	NPD6100	Approved
0.8171	Intermediate Similarity	NPD7768	Phase 2
0.8121	Intermediate Similarity	NPD3749	Approved
0.8113	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7473	Discontinued
0.8063	Intermediate Similarity	NPD6273	Approved
0.8037	Intermediate Similarity	NPD7411	Suspended
0.8036	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.7988	Intermediate Similarity	NPD37	Approved
0.7977	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD7003	Approved
0.7964	Intermediate Similarity	NPD6234	Discontinued
0.7962	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7228	Approved
0.7952	Intermediate Similarity	NPD4966	Approved
0.7952	Intermediate Similarity	NPD4967	Phase 2
0.7952	Intermediate Similarity	NPD4965	Approved
0.7939	Intermediate Similarity	NPD1465	Phase 2
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5710	Approved
0.7929	Intermediate Similarity	NPD7229	Phase 3
0.7929	Intermediate Similarity	NPD5711	Approved
0.7917	Intermediate Similarity	NPD5494	Approved
0.7914	Intermediate Similarity	NPD3226	Approved
0.7911	Intermediate Similarity	NPD2800	Approved
0.7898	Intermediate Similarity	NPD2346	Discontinued
0.7886	Intermediate Similarity	NPD8313	Approved
0.7886	Intermediate Similarity	NPD8312	Approved
0.7885	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD4628	Phase 3
0.7843	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4380	Phase 2
0.7758	Intermediate Similarity	NPD6599	Discontinued
0.7736	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3764	Approved
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7714	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7458	Discontinued
0.7697	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5124	Phase 1
0.7673	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1934	Approved
0.7665	Intermediate Similarity	NPD6801	Discontinued
0.7662	Intermediate Similarity	NPD4625	Phase 3
0.7661	Intermediate Similarity	NPD8127	Discontinued
0.7619	Intermediate Similarity	NPD5760	Phase 2
0.7619	Intermediate Similarity	NPD5761	Phase 2
0.7613	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7588	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD920	Approved
0.7574	Intermediate Similarity	NPD5402	Approved
0.7571	Intermediate Similarity	NPD7240	Approved
0.7566	Intermediate Similarity	NPD6696	Suspended
0.7556	Intermediate Similarity	NPD8434	Phase 2
0.7547	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2799	Discontinued
0.7543	Intermediate Similarity	NPD3818	Discontinued
0.7529	Intermediate Similarity	NPD3882	Suspended
0.7529	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7473	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7458	Intermediate Similarity	NPD7074	Phase 3
0.7457	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8032	Phase 2
0.7443	Intermediate Similarity	NPD7177	Discontinued
0.7438	Intermediate Similarity	NPD4308	Phase 3
0.7438	Intermediate Similarity	NPD1510	Phase 2
0.7421	Intermediate Similarity	NPD6651	Approved
0.7421	Intermediate Similarity	NPD1607	Approved
0.7412	Intermediate Similarity	NPD2801	Approved
0.7405	Intermediate Similarity	NPD4140	Approved
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7401	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD7390	Discontinued
0.7394	Intermediate Similarity	NPD6799	Approved
0.7371	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7368	Intermediate Similarity	NPD4288	Approved
0.7368	Intermediate Similarity	NPD3817	Phase 2
0.7365	Intermediate Similarity	NPD5403	Approved
0.7362	Intermediate Similarity	NPD1243	Approved
0.736	Intermediate Similarity	NPD7472	Approved
0.7358	Intermediate Similarity	NPD230	Phase 1
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7355	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6002	Phase 3
0.7346	Intermediate Similarity	NPD6005	Phase 3
0.7346	Intermediate Similarity	NPD6004	Phase 3
0.7346	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6663	Approved
0.7338	Intermediate Similarity	NPD1283	Approved
0.7333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8166	Discontinued
0.731	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD5736	Approved
0.7296	Intermediate Similarity	NPD4060	Phase 1
0.7296	Intermediate Similarity	NPD1240	Approved
0.7296	Intermediate Similarity	NPD2979	Phase 3
0.729	Intermediate Similarity	NPD2797	Approved
0.7289	Intermediate Similarity	NPD1511	Approved
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7278	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7278	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6674	Discontinued
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.725	Intermediate Similarity	NPD6355	Discontinued
0.7247	Intermediate Similarity	NPD3751	Discontinued
0.7246	Intermediate Similarity	NPD5401	Approved
0.7238	Intermediate Similarity	NPD7808	Phase 3
0.7237	Intermediate Similarity	NPD4626	Approved
0.7229	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6823	Phase 2
0.7222	Intermediate Similarity	NPD6797	Phase 2
0.7222	Intermediate Similarity	NPD5953	Discontinued
0.7215	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6777	Approved
0.7211	Intermediate Similarity	NPD6782	Approved
0.7211	Intermediate Similarity	NPD6780	Approved
0.7211	Intermediate Similarity	NPD6781	Approved
0.7211	Intermediate Similarity	NPD6779	Approved
0.7211	Intermediate Similarity	NPD6776	Approved
0.7211	Intermediate Similarity	NPD6778	Approved
0.7202	Intermediate Similarity	NPD1512	Approved
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7189	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD4307	Phase 2
0.7188	Intermediate Similarity	NPD7697	Approved
0.7188	Intermediate Similarity	NPD7698	Approved
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7178	Intermediate Similarity	NPD2438	Suspended
0.7171	Intermediate Similarity	NPD5691	Approved
0.717	Intermediate Similarity	NPD7985	Registered
0.717	Intermediate Similarity	NPD3268	Approved
0.7158	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7134	Intermediate Similarity	NPD5763	Approved
0.7134	Intermediate Similarity	NPD5762	Approved
0.7126	Intermediate Similarity	NPD7236	Approved
0.7124	Intermediate Similarity	NPD1778	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7117	Intermediate Similarity	NPD7033	Discontinued
0.7108	Intermediate Similarity	NPD4110	Phase 3
0.7108	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7095	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