NPASS Compound

Structure

NPC472074 OpenBabel07101718282D 35 38 0 0 1 0 0 0 0 0999 V2000 2.1800 -2.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7019 0.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0811 -0.1541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7419 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8507 0.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0539 -1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9199 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8678 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2396 -0.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 -1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6117 0.7911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 -1.1575 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1878 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 0.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 -1.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5531 0.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9199 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5232 -0.5458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9559 -1.0108 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0539 0.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0902 -0.0199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8964 -2.3810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3793 1.0171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7859 0.9253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7470 -1.6225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2991 0.5919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 10 1 0 0 0 0 10 21 2 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 19 2 0 0 0 0 13 29 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 1 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 9 1 6 0 0 0 20 27 1 0 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 25 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 0 0 0 0 24 33 1 6 0 0 0 25 29 1 6 0 0 0 26 28 1 0 0 0 0 26 34 1 6 0 0 0 28 35 1 0 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	523.979
LogP:	3.705
LogD:	2.541
LogS:	-3.328
# Rotatable Bonds:	5
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	5.556
Fsp3:	0.733
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:	-4.733
MDCK Permeability:	2.0832381778745912e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.233
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.714
Plasma Protein Binding (PPB):	85.61898040771484%
Volume Distribution (VD):	0.81
Pgp-substrate:	8.381422996520996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.295
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	5.515
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.481
Carcinogencity:	0.609
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC472074

Natural Product ID:	NPC472074
*Common Name:**	BLFKBZDMCGJGMK-GDKAECDTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BLFKBZDMCGJGMK-GDKAECDTSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-17(14-22(31)26(34)28(4,5)35)25-23(32)16-30(7)21-10-9-20-18(8-11-24(33)27(20,2)3)15-19(21)12-13-29(25,30)6/h8,10,12,17,20,24-26,33-35H,9,11,13-16H2,1-7H3/t17-,20-,24+,25+,26-,29-,30+/m1/s1
SMILES:	CC(CC(=O)C(C(C)(C)O)O)C1C(=O)CC2(C1(CC=C3C2=CCC4C(=CCC(C4(C)C)O)C3)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337543
PubChem CID:	n.a.
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
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	aerial part	n.a.	PMID[19280146]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	rhizomes	n.a.	n.a.	PMID[25136911]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[570151]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[570151]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[570151]

☑ 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 NPC472074 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	198
0.1-0.2	1132
0.2-0.3	5395
0.3-0.4	15397
0.4-0.5	9265
0.5-0.6	7962
0.6-0.7	2983
0.7-0.8	361
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472073
0.8557	High Similarity	NPC473161
0.8495	Intermediate Similarity	NPC44181
0.8478	Intermediate Similarity	NPC89077
0.8404	Intermediate Similarity	NPC32830
0.8404	Intermediate Similarity	NPC474245
0.828	Intermediate Similarity	NPC51014
0.828	Intermediate Similarity	NPC473168
0.8211	Intermediate Similarity	NPC76879
0.82	Intermediate Similarity	NPC110149
0.8191	Intermediate Similarity	NPC90652
0.8191	Intermediate Similarity	NPC99909
0.8105	Intermediate Similarity	NPC470417
0.8105	Intermediate Similarity	NPC328313
0.81	Intermediate Similarity	NPC147954
0.8065	Intermediate Similarity	NPC59453
0.8065	Intermediate Similarity	NPC221758
0.8041	Intermediate Similarity	NPC19114
0.8018	Intermediate Similarity	NPC472075
0.8018	Intermediate Similarity	NPC472076
0.8	Intermediate Similarity	NPC43747
0.8	Intermediate Similarity	NPC138756
0.7981	Intermediate Similarity	NPC166607
0.798	Intermediate Similarity	NPC263347
0.798	Intermediate Similarity	NPC127063
0.7959	Intermediate Similarity	NPC472942
0.7957	Intermediate Similarity	NPC476082
0.7957	Intermediate Similarity	NPC278648
0.7938	Intermediate Similarity	NPC129913
0.7938	Intermediate Similarity	NPC69622
0.7917	Intermediate Similarity	NPC471722
0.7917	Intermediate Similarity	NPC471724
0.7917	Intermediate Similarity	NPC53911
0.7905	Intermediate Similarity	NPC165873
0.79	Intermediate Similarity	NPC473164
0.7895	Intermediate Similarity	NPC31564
0.7895	Intermediate Similarity	NPC118648
0.7895	Intermediate Similarity	NPC222613
0.7895	Intermediate Similarity	NPC474733
0.7895	Intermediate Similarity	NPC475022
0.7895	Intermediate Similarity	NPC145879
0.7895	Intermediate Similarity	NPC474778
0.7895	Intermediate Similarity	NPC474732
0.7895	Intermediate Similarity	NPC20688
0.7885	Intermediate Similarity	NPC160843
0.7879	Intermediate Similarity	NPC196485
0.7879	Intermediate Similarity	NPC245972
0.7872	Intermediate Similarity	NPC473246
0.7849	Intermediate Similarity	NPC151519
0.7835	Intermediate Similarity	NPC84271
0.7835	Intermediate Similarity	NPC31985
0.7835	Intermediate Similarity	NPC77168
0.7835	Intermediate Similarity	NPC102414
0.7835	Intermediate Similarity	NPC1015
0.7822	Intermediate Similarity	NPC474938
0.7822	Intermediate Similarity	NPC469432
0.7822	Intermediate Similarity	NPC474785
0.7812	Intermediate Similarity	NPC58063
0.7812	Intermediate Similarity	NPC472484
0.7812	Intermediate Similarity	NPC472481
0.7812	Intermediate Similarity	NPC475740
0.7812	Intermediate Similarity	NPC136548
0.7812	Intermediate Similarity	NPC96496
0.7812	Intermediate Similarity	NPC472482
0.781	Intermediate Similarity	NPC475494
0.7807	Intermediate Similarity	NPC472078
0.7807	Intermediate Similarity	NPC472077
0.78	Intermediate Similarity	NPC280725
0.7789	Intermediate Similarity	NPC79573
0.7789	Intermediate Similarity	NPC202868
0.7789	Intermediate Similarity	NPC474083
0.7788	Intermediate Similarity	NPC191892
0.7788	Intermediate Similarity	NPC117185
0.7788	Intermediate Similarity	NPC475050
0.7778	Intermediate Similarity	NPC66429
0.7778	Intermediate Similarity	NPC477520
0.7778	Intermediate Similarity	NPC152897
0.7778	Intermediate Similarity	NPC233118
0.7778	Intermediate Similarity	NPC250575
0.7766	Intermediate Similarity	NPC477373
0.7755	Intermediate Similarity	NPC136801
0.7755	Intermediate Similarity	NPC46281
0.7745	Intermediate Similarity	NPC191565
0.7742	Intermediate Similarity	NPC136150
0.7736	Intermediate Similarity	NPC58370
0.7736	Intermediate Similarity	NPC43285
0.7732	Intermediate Similarity	NPC247406
0.7732	Intermediate Similarity	NPC48866
0.7732	Intermediate Similarity	NPC242864
0.7723	Intermediate Similarity	NPC328162
0.7723	Intermediate Similarity	NPC305483
0.7723	Intermediate Similarity	NPC155676
0.7723	Intermediate Similarity	NPC96859
0.7708	Intermediate Similarity	NPC94755
0.7708	Intermediate Similarity	NPC472491
0.7708	Intermediate Similarity	NPC472494
0.7708	Intermediate Similarity	NPC155011
0.7708	Intermediate Similarity	NPC72133
0.77	Intermediate Similarity	NPC473172
0.77	Intermediate Similarity	NPC469406
0.77	Intermediate Similarity	NPC67831
0.77	Intermediate Similarity	NPC318332
0.77	Intermediate Similarity	NPC174051
0.7692	Intermediate Similarity	NPC473424
0.7692	Intermediate Similarity	NPC325946
0.7684	Intermediate Similarity	NPC237712
0.7684	Intermediate Similarity	NPC214043
0.7684	Intermediate Similarity	NPC85774
0.7684	Intermediate Similarity	NPC82902
0.7677	Intermediate Similarity	NPC45269
0.7677	Intermediate Similarity	NPC168027
0.7677	Intermediate Similarity	NPC262870
0.7677	Intermediate Similarity	NPC185936
0.7677	Intermediate Similarity	NPC473167
0.7677	Intermediate Similarity	NPC189520
0.767	Intermediate Similarity	NPC316964
0.766	Intermediate Similarity	NPC212083
0.7653	Intermediate Similarity	NPC310010
0.7653	Intermediate Similarity	NPC472970
0.7653	Intermediate Similarity	NPC86319
0.7653	Intermediate Similarity	NPC268406
0.7653	Intermediate Similarity	NPC472971
0.7653	Intermediate Similarity	NPC186688
0.7653	Intermediate Similarity	NPC275740
0.7653	Intermediate Similarity	NPC326627
0.7653	Intermediate Similarity	NPC26959
0.7647	Intermediate Similarity	NPC161147
0.7647	Intermediate Similarity	NPC471815
0.7629	Intermediate Similarity	NPC317590
0.7629	Intermediate Similarity	NPC159046
0.7629	Intermediate Similarity	NPC312215
0.7629	Intermediate Similarity	NPC233836
0.7629	Intermediate Similarity	NPC141292
0.7629	Intermediate Similarity	NPC187376
0.7624	Intermediate Similarity	NPC45324
0.7624	Intermediate Similarity	NPC200702
0.7624	Intermediate Similarity	NPC473170
0.7624	Intermediate Similarity	NPC162001
0.7624	Intermediate Similarity	NPC472485
0.7624	Intermediate Similarity	NPC88310
0.7624	Intermediate Similarity	NPC222845
0.7615	Intermediate Similarity	NPC472928
0.7604	Intermediate Similarity	NPC471224
0.7604	Intermediate Similarity	NPC469948
0.7604	Intermediate Similarity	NPC474218
0.76	Intermediate Similarity	NPC134826
0.76	Intermediate Similarity	NPC12722
0.76	Intermediate Similarity	NPC474736
0.76	Intermediate Similarity	NPC474807
0.7593	Intermediate Similarity	NPC470257
0.7579	Intermediate Similarity	NPC83569
0.7579	Intermediate Similarity	NPC310470
0.7579	Intermediate Similarity	NPC69279
0.7576	Intermediate Similarity	NPC469400
0.7576	Intermediate Similarity	NPC48010
0.7576	Intermediate Similarity	NPC123854
0.7576	Intermediate Similarity	NPC320026
0.7576	Intermediate Similarity	NPC171441
0.7576	Intermediate Similarity	NPC289213
0.7576	Intermediate Similarity	NPC191684
0.7573	Intermediate Similarity	NPC235464
0.7573	Intermediate Similarity	NPC153776
0.7573	Intermediate Similarity	NPC472729
0.7573	Intermediate Similarity	NPC472730
0.7573	Intermediate Similarity	NPC177680
0.7573	Intermediate Similarity	NPC166745
0.7573	Intermediate Similarity	NPC186810
0.757	Intermediate Similarity	NPC330011
0.757	Intermediate Similarity	NPC329048
0.757	Intermediate Similarity	NPC473169
0.757	Intermediate Similarity	NPC472925
0.757	Intermediate Similarity	NPC473284
0.757	Intermediate Similarity	NPC185
0.7568	Intermediate Similarity	NPC473898
0.7553	Intermediate Similarity	NPC14151
0.7553	Intermediate Similarity	NPC6707
0.7551	Intermediate Similarity	NPC472483
0.7551	Intermediate Similarity	NPC131470
0.7551	Intermediate Similarity	NPC294480
0.7551	Intermediate Similarity	NPC143767
0.7551	Intermediate Similarity	NPC292491
0.7551	Intermediate Similarity	NPC310752
0.7551	Intermediate Similarity	NPC193360
0.7549	Intermediate Similarity	NPC269492
0.7549	Intermediate Similarity	NPC472941
0.7549	Intermediate Similarity	NPC456
0.7549	Intermediate Similarity	NPC120708
0.7549	Intermediate Similarity	NPC471463
0.7549	Intermediate Similarity	NPC21681
0.7549	Intermediate Similarity	NPC117133
0.7549	Intermediate Similarity	NPC249954
0.7549	Intermediate Similarity	NPC471153
0.7549	Intermediate Similarity	NPC472675
0.7549	Intermediate Similarity	NPC49371
0.7547	Intermediate Similarity	NPC477812
0.7547	Intermediate Similarity	NPC13385
0.7527	Intermediate Similarity	NPC274996
0.7527	Intermediate Similarity	NPC196827
0.7527	Intermediate Similarity	NPC328714
0.7526	Intermediate Similarity	NPC212843

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 NPC472074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1664
0.2-0.3	4044
0.3-0.4	2336
0.4-0.5	527
0.5-0.6	198
0.6-0.7	194
0.7-0.8	15
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
0.8085	Intermediate Similarity	NPD5279	Phase 3
0.8065	Intermediate Similarity	NPD4786	Approved
0.7849	Intermediate Similarity	NPD3667	Approved
0.7708	Intermediate Similarity	NPD4694	Approved
0.7708	Intermediate Similarity	NPD5280	Approved
0.7653	Intermediate Similarity	NPD4753	Phase 2
0.7624	Intermediate Similarity	NPD4629	Approved
0.7624	Intermediate Similarity	NPD5210	Approved
0.7476	Intermediate Similarity	NPD4755	Approved
0.7475	Intermediate Similarity	NPD5328	Approved
0.7426	Intermediate Similarity	NPD6399	Phase 3
0.7423	Intermediate Similarity	NPD5329	Approved
0.7391	Intermediate Similarity	NPD6933	Approved
0.7379	Intermediate Similarity	NPD5221	Approved
0.7379	Intermediate Similarity	NPD5222	Approved
0.7379	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4697	Phase 3
0.7364	Intermediate Similarity	NPD4634	Approved
0.7347	Intermediate Similarity	NPD3618	Phase 1
0.7347	Intermediate Similarity	NPD5690	Phase 2
0.7333	Intermediate Similarity	NPD5285	Approved
0.7333	Intermediate Similarity	NPD5286	Approved
0.7333	Intermediate Similarity	NPD4700	Approved
0.7333	Intermediate Similarity	NPD4696	Approved
0.7327	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD3665	Phase 1
0.732	Intermediate Similarity	NPD3666	Approved
0.732	Intermediate Similarity	NPD3133	Approved
0.732	Intermediate Similarity	NPD3668	Phase 3
0.732	Intermediate Similarity	NPD4197	Approved
0.7308	Intermediate Similarity	NPD6084	Phase 2
0.7308	Intermediate Similarity	NPD6083	Phase 2
0.7308	Intermediate Similarity	NPD5173	Approved
0.7282	Intermediate Similarity	NPD5695	Phase 3
0.7264	Intermediate Similarity	NPD5223	Approved
0.7263	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4202	Approved
0.7238	Intermediate Similarity	NPD5696	Approved
0.7196	Intermediate Similarity	NPD4633	Approved
0.7196	Intermediate Similarity	NPD5224	Approved
0.7196	Intermediate Similarity	NPD5225	Approved
0.7196	Intermediate Similarity	NPD5226	Approved
0.7196	Intermediate Similarity	NPD5211	Phase 2
0.7174	Intermediate Similarity	NPD6926	Approved
0.7174	Intermediate Similarity	NPD6924	Approved
0.7157	Intermediate Similarity	NPD6050	Approved
0.7157	Intermediate Similarity	NPD5281	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.7157	Intermediate Similarity	NPD5284	Approved
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.713	Intermediate Similarity	NPD4754	Approved
0.713	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD5175	Approved
0.7113	Intermediate Similarity	NPD4221	Approved
0.7113	Intermediate Similarity	NPD4223	Phase 3
0.7097	Intermediate Similarity	NPD7339	Approved
0.7097	Intermediate Similarity	NPD6942	Approved
0.7087	Intermediate Similarity	NPD5133	Approved
0.7064	Intermediate Similarity	NPD5141	Approved
0.7059	Intermediate Similarity	NPD5692	Phase 3
0.703	Intermediate Similarity	NPD4518	Approved
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6672	Approved
0.7027	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD7320	Approved
0.7027	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD4768	Approved
0.699	Remote Similarity	NPD5694	Approved
0.6983	Remote Similarity	NPD7115	Discovery
0.6964	Remote Similarity	NPD6372	Approved
0.6964	Remote Similarity	NPD6373	Approved
0.6961	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6101	Approved
0.6961	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5701	Approved
0.6937	Remote Similarity	NPD5697	Approved
0.693	Remote Similarity	NPD8297	Approved
0.6907	Remote Similarity	NPD4695	Discontinued
0.6907	Remote Similarity	NPD7525	Registered
0.6903	Remote Similarity	NPD7290	Approved
0.6903	Remote Similarity	NPD7102	Approved
0.6903	Remote Similarity	NPD6883	Approved
0.6893	Remote Similarity	NPD4096	Approved
0.6875	Remote Similarity	NPD3617	Approved
0.6875	Remote Similarity	NPD4729	Approved
0.6875	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD5128	Approved
0.6875	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD4632	Approved
0.6869	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6869	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD6650	Approved
0.6842	Remote Similarity	NPD8130	Phase 1
0.6842	Remote Similarity	NPD6617	Approved
0.6842	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5369	Approved
0.6837	Remote Similarity	NPD4692	Approved
0.6837	Remote Similarity	NPD4139	Approved
0.6832	Remote Similarity	NPD4693	Phase 3
0.6832	Remote Similarity	NPD4689	Approved
0.6832	Remote Similarity	NPD6098	Approved
0.6832	Remote Similarity	NPD4138	Approved
0.6832	Remote Similarity	NPD4688	Approved
0.6832	Remote Similarity	NPD5205	Approved
0.6832	Remote Similarity	NPD4690	Approved
0.6827	Remote Similarity	NPD7515	Phase 2
0.6814	Remote Similarity	NPD6014	Approved
0.6814	Remote Similarity	NPD6013	Approved
0.6814	Remote Similarity	NPD6012	Approved
0.6809	Remote Similarity	NPD5733	Approved
0.6807	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD6904	Approved
0.6783	Remote Similarity	NPD6882	Approved
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6765	Remote Similarity	NPD7524	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6754	Remote Similarity	NPD5249	Phase 3
0.6754	Remote Similarity	NPD5247	Approved
0.6754	Remote Similarity	NPD5169	Approved
0.6754	Remote Similarity	NPD5135	Approved
0.6754	Remote Similarity	NPD5250	Approved
0.6754	Remote Similarity	NPD5251	Approved
0.6754	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5248	Approved
0.6739	Remote Similarity	NPD6922	Approved
0.6739	Remote Similarity	NPD6923	Approved
0.6735	Remote Similarity	NPD6930	Phase 2
0.6735	Remote Similarity	NPD6931	Approved
0.6733	Remote Similarity	NPD1696	Phase 3
0.6733	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5091	Approved
0.6726	Remote Similarity	NPD5168	Approved
0.6723	Remote Similarity	NPD4522	Approved
0.6701	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6695	Phase 3
0.6696	Remote Similarity	NPD5217	Approved
0.6696	Remote Similarity	NPD5215	Approved
0.6696	Remote Similarity	NPD5216	Approved
0.6696	Remote Similarity	NPD5127	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6637	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD5654	Approved
0.6634	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6929	Approved
0.6632	Remote Similarity	NPD4687	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.66	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD4270	Approved
0.6598	Remote Similarity	NPD6932	Approved
0.6596	Remote Similarity	NPD5276	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6571	Remote Similarity	NPD5207	Approved
0.6566	Remote Similarity	NPD4748	Discontinued
0.6566	Remote Similarity	NPD7509	Discontinued
0.6562	Remote Similarity	NPD8264	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6009	Approved
0.6542	Remote Similarity	NPD5282	Discontinued
0.6542	Remote Similarity	NPD7748	Approved
0.6538	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6903	Approved
0.6532	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD5167	Approved
0.6514	Remote Similarity	NPD5959	Approved
0.6509	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD6335	Approved
0.6489	Remote Similarity	NPD4789	Approved
0.648	Remote Similarity	NPD7078	Approved
0.648	Remote Similarity	NPD8293	Discontinued
0.6471	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD6868	Approved
0.6465	Remote Similarity	NPD6683	Phase 2
0.6465	Remote Similarity	NPD4195	Approved
0.6458	Remote Similarity	NPD4784	Approved
0.6458	Remote Similarity	NPD4785	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