NPASS Compound

Structure

NPC476038 OpenBabel07101718192D 33 36 0 0 1 0 0 0 0 0999 V2000 4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5446 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9703 2.4680 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 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 2.6831 -0.3090 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 0.8660 1.5000 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 -3.0000 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 5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2601 0.0000 C 0 0 2 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 2.6831 1.3090 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 -0.8660 -0.5000 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 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 22 2 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 2 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 21 3 1 6 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 27 1 1 0 0 0 24 29 1 1 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 26 32 2 0 0 0 0 26 33 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 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	6.484
LogD:	4.877
LogS:	-4.722
# Rotatable Bonds:	9
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	5.384
Fsp3:	0.833
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:	-5.42
MDCK Permeability:	4.688015451392857e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	96.92543029785156%
Volume Distribution (VD):	0.586
Pgp-substrate:	1.904565453529358%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.549
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	4.131
Half-life (T1/2):	0.534

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.488
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.947
Carcinogencity:	0.205
Eye Corrosion:	0.024
Eye Irritation:	0.512
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC476038

Natural Product ID:	NPC476038
*Common Name:**	Secaubryenol
IUPAC Name:	n.a.
Synonyms:	Secaubryenol
Standard InCHIKey:	JFCYFLMAPFEZKC-XDPIHHSESA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-20(2)8-7-9-21(3)23-12-14-28(6)25-11-10-24(22(4)18-31)29(15-13-26(32)33)19-30(25,29)17-16-27(23,28)5/h8,21,23-25,31H,4,7,9-19H2,1-3,5-6H3,(H,32,33)/t21-,23-,24+,25-,27-,28+,29-,30+/m1/s1
SMILES:	OCC(=C)[C@@H]1CC[C@H]2[C@]3([C@]1(CCC(=O)O)C3)CC[C@]1([C@@]2(C)CC[C@@H]1[C@@H](CCC=C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523126
PubChem CID:	44566394
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
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190447]
NPO11647	Gardenia sootepensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19456120]
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11647	Gardenia sootepensis	Species	Rubiaceae	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	9

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[489022]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	100000.0	nM	PMID[489022]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[489022]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[489022]
NPT845	Cell Line	BT-474	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[489023]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[489023]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[489023]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[489023]

☑ 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 NPC476038 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	151
0.1-0.2	1051
0.2-0.3	5743
0.3-0.4	15851
0.4-0.5	6811
0.5-0.6	6705
0.6-0.7	4667
0.7-0.8	1576
0.8-0.85	100
0.85-0.9	29
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194937
0.9873	High Similarity	NPC283733
0.9359	High Similarity	NPC158846
0.9259	High Similarity	NPC165064
0.9176	High Similarity	NPC476187
0.9036	High Similarity	NPC186975
0.8987	High Similarity	NPC239098
0.8953	High Similarity	NPC470113
0.8941	High Similarity	NPC66344
0.8941	High Similarity	NPC128496
0.8929	High Similarity	NPC236618
0.8902	High Similarity	NPC215893
0.8864	High Similarity	NPC476174
0.8824	High Similarity	NPC117122
0.881	High Similarity	NPC155011
0.881	High Similarity	NPC475007
0.881	High Similarity	NPC70661
0.8764	High Similarity	NPC29152
0.8706	High Similarity	NPC474684
0.8706	High Similarity	NPC142361
0.8706	High Similarity	NPC96496
0.8706	High Similarity	NPC128644
0.869	High Similarity	NPC471224
0.869	High Similarity	NPC269638
0.8667	High Similarity	NPC156546
0.8659	High Similarity	NPC147066
0.8652	High Similarity	NPC293052
0.8642	High Similarity	NPC477371
0.8588	High Similarity	NPC469994
0.8571	High Similarity	NPC164577
0.8571	High Similarity	NPC19849
0.8571	High Similarity	NPC472864
0.8554	High Similarity	NPC477858
0.8519	High Similarity	NPC321690
0.8506	High Similarity	NPC475921
0.8506	High Similarity	NPC474704
0.85	High Similarity	NPC20466
0.8488	Intermediate Similarity	NPC187376
0.8488	Intermediate Similarity	NPC136948
0.8488	Intermediate Similarity	NPC159046
0.8488	Intermediate Similarity	NPC233836
0.8471	Intermediate Similarity	NPC474083
0.8452	Intermediate Similarity	NPC167103
0.8452	Intermediate Similarity	NPC97913
0.8434	Intermediate Similarity	NPC477372
0.8434	Intermediate Similarity	NPC38350
0.8434	Intermediate Similarity	NPC201912
0.8427	Intermediate Similarity	NPC477855
0.8409	Intermediate Similarity	NPC469400
0.8391	Intermediate Similarity	NPC472870
0.8372	Intermediate Similarity	NPC472869
0.8372	Intermediate Similarity	NPC55309
0.8372	Intermediate Similarity	NPC28252
0.8353	Intermediate Similarity	NPC59453
0.8353	Intermediate Similarity	NPC85774
0.8353	Intermediate Similarity	NPC214043
0.8353	Intermediate Similarity	NPC263974
0.8353	Intermediate Similarity	NPC82902
0.8353	Intermediate Similarity	NPC221758
0.8353	Intermediate Similarity	NPC472865
0.8333	Intermediate Similarity	NPC91369
0.8333	Intermediate Similarity	NPC124207
0.8333	Intermediate Similarity	NPC133391
0.8333	Intermediate Similarity	NPC170985
0.8333	Intermediate Similarity	NPC260956
0.8333	Intermediate Similarity	NPC469406
0.8333	Intermediate Similarity	NPC320514
0.8315	Intermediate Similarity	NPC189520
0.8315	Intermediate Similarity	NPC110923
0.8315	Intermediate Similarity	NPC154101
0.8315	Intermediate Similarity	NPC74296
0.8295	Intermediate Similarity	NPC2983
0.8295	Intermediate Similarity	NPC476733
0.8295	Intermediate Similarity	NPC262043
0.8295	Intermediate Similarity	NPC77168
0.8295	Intermediate Similarity	NPC84271
0.8295	Intermediate Similarity	NPC102414
0.8295	Intermediate Similarity	NPC215029
0.8295	Intermediate Similarity	NPC155479
0.8295	Intermediate Similarity	NPC474570
0.8295	Intermediate Similarity	NPC214387
0.8295	Intermediate Similarity	NPC473999
0.8295	Intermediate Similarity	NPC309603
0.8293	Intermediate Similarity	NPC179028
0.828	Intermediate Similarity	NPC470074
0.8276	Intermediate Similarity	NPC312215
0.8276	Intermediate Similarity	NPC167877
0.8276	Intermediate Similarity	NPC317590
0.8272	Intermediate Similarity	NPC246445
0.8261	Intermediate Similarity	NPC475894
0.8261	Intermediate Similarity	NPC107243
0.8256	Intermediate Similarity	NPC29447
0.8256	Intermediate Similarity	NPC474218
0.8256	Intermediate Similarity	NPC469948
0.8256	Intermediate Similarity	NPC202868
0.8242	Intermediate Similarity	NPC84383
0.8235	Intermediate Similarity	NPC83569
0.8235	Intermediate Similarity	NPC477373
0.8235	Intermediate Similarity	NPC310470
0.8235	Intermediate Similarity	NPC69279
0.8235	Intermediate Similarity	NPC245866
0.8228	Intermediate Similarity	NPC160817
0.8222	Intermediate Similarity	NPC470224
0.8222	Intermediate Similarity	NPC470375
0.8222	Intermediate Similarity	NPC243866
0.8222	Intermediate Similarity	NPC476304
0.8222	Intermediate Similarity	NPC470376
0.8214	Intermediate Similarity	NPC103754
0.8214	Intermediate Similarity	NPC229584
0.8214	Intermediate Similarity	NPC14203
0.8214	Intermediate Similarity	NPC474484
0.8211	Intermediate Similarity	NPC476237
0.8202	Intermediate Similarity	NPC477147
0.8202	Intermediate Similarity	NPC477149
0.8202	Intermediate Similarity	NPC471896
0.8202	Intermediate Similarity	NPC48010
0.8193	Intermediate Similarity	NPC215843
0.8193	Intermediate Similarity	NPC274996
0.8193	Intermediate Similarity	NPC196827
0.8193	Intermediate Similarity	NPC327674
0.8182	Intermediate Similarity	NPC16377
0.8182	Intermediate Similarity	NPC242864
0.8182	Intermediate Similarity	NPC146937
0.8182	Intermediate Similarity	NPC294480
0.8172	Intermediate Similarity	NPC98868
0.8171	Intermediate Similarity	NPC471899
0.8171	Intermediate Similarity	NPC107039
0.8171	Intermediate Similarity	NPC471897
0.8171	Intermediate Similarity	NPC68828
0.8171	Intermediate Similarity	NPC66105
0.8171	Intermediate Similarity	NPC61952
0.8161	Intermediate Similarity	NPC474732
0.8161	Intermediate Similarity	NPC31564
0.8161	Intermediate Similarity	NPC145879
0.8161	Intermediate Similarity	NPC82979
0.8161	Intermediate Similarity	NPC322159
0.8161	Intermediate Similarity	NPC51014
0.8161	Intermediate Similarity	NPC474733
0.8161	Intermediate Similarity	NPC474778
0.8161	Intermediate Similarity	NPC212843
0.8152	Intermediate Similarity	NPC327788
0.8152	Intermediate Similarity	NPC235053
0.8152	Intermediate Similarity	NPC250757
0.8152	Intermediate Similarity	NPC301534
0.8152	Intermediate Similarity	NPC472941
0.8152	Intermediate Similarity	NPC456
0.8152	Intermediate Similarity	NPC155676
0.8148	Intermediate Similarity	NPC476844
0.8148	Intermediate Similarity	NPC192540
0.8148	Intermediate Similarity	NPC279666
0.8148	Intermediate Similarity	NPC476795
0.814	Intermediate Similarity	NPC237712
0.814	Intermediate Similarity	NPC178025
0.814	Intermediate Similarity	NPC473246
0.814	Intermediate Similarity	NPC181743
0.814	Intermediate Similarity	NPC16287
0.814	Intermediate Similarity	NPC248758
0.8132	Intermediate Similarity	NPC476186
0.8125	Intermediate Similarity	NPC330659
0.8125	Intermediate Similarity	NPC161187
0.8125	Intermediate Similarity	NPC244708
0.8118	Intermediate Similarity	NPC151519
0.8118	Intermediate Similarity	NPC145143
0.8118	Intermediate Similarity	NPC296367
0.8111	Intermediate Similarity	NPC212301
0.8111	Intermediate Similarity	NPC110657
0.8111	Intermediate Similarity	NPC473998
0.8111	Intermediate Similarity	NPC23217
0.8111	Intermediate Similarity	NPC45269
0.8111	Intermediate Similarity	NPC475806
0.8111	Intermediate Similarity	NPC473986
0.8111	Intermediate Similarity	NPC474018
0.8111	Intermediate Similarity	NPC86266
0.8095	Intermediate Similarity	NPC472478
0.8095	Intermediate Similarity	NPC104545
0.809	Intermediate Similarity	NPC262858
0.809	Intermediate Similarity	NPC310236
0.809	Intermediate Similarity	NPC174342
0.809	Intermediate Similarity	NPC54689
0.809	Intermediate Similarity	NPC281524
0.809	Intermediate Similarity	NPC146554
0.809	Intermediate Similarity	NPC472240
0.8085	Intermediate Similarity	NPC218383
0.8085	Intermediate Similarity	NPC477521
0.8085	Intermediate Similarity	NPC476303
0.8077	Intermediate Similarity	NPC160209
0.8072	Intermediate Similarity	NPC269543
0.8072	Intermediate Similarity	NPC297996
0.8072	Intermediate Similarity	NPC260385
0.8072	Intermediate Similarity	NPC321514
0.8072	Intermediate Similarity	NPC59436
0.8072	Intermediate Similarity	NPC280654
0.8072	Intermediate Similarity	NPC110094
0.8072	Intermediate Similarity	NPC82635
0.8072	Intermediate Similarity	NPC198240
0.8072	Intermediate Similarity	NPC247783
0.8068	Intermediate Similarity	NPC90652
0.8068	Intermediate Similarity	NPC58063
0.8068	Intermediate Similarity	NPC475740
0.8068	Intermediate Similarity	NPC93778

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 NPC476038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1422
0.2-0.3	4138
0.3-0.4	2362
0.4-0.5	589
0.5-0.6	202
0.6-0.7	198
0.7-0.8	100
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8353	Intermediate Similarity	NPD4786	Approved
0.8118	Intermediate Similarity	NPD3667	Approved
0.8046	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD6399	Phase 3
0.7931	Intermediate Similarity	NPD3666	Approved
0.7931	Intermediate Similarity	NPD3133	Approved
0.7931	Intermediate Similarity	NPD3665	Phase 1
0.7889	Intermediate Similarity	NPD5328	Approved
0.7872	Intermediate Similarity	NPD6084	Phase 2
0.7872	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7753	Intermediate Similarity	NPD7146	Approved
0.7753	Intermediate Similarity	NPD7334	Approved
0.7753	Intermediate Similarity	NPD7521	Approved
0.7753	Intermediate Similarity	NPD3618	Phase 1
0.7753	Intermediate Similarity	NPD6409	Approved
0.7753	Intermediate Similarity	NPD6684	Approved
0.7753	Intermediate Similarity	NPD5330	Approved
0.7717	Intermediate Similarity	NPD6079	Approved
0.7701	Intermediate Similarity	NPD4221	Approved
0.7701	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD4753	Phase 2
0.764	Intermediate Similarity	NPD5329	Approved
0.7614	Intermediate Similarity	NPD4788	Approved
0.7582	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6903	Approved
0.7556	Intermediate Similarity	NPD6098	Approved
0.7556	Intermediate Similarity	NPD5279	Phase 3
0.7528	Intermediate Similarity	NPD4197	Approved
0.7527	Intermediate Similarity	NPD7515	Phase 2
0.7526	Intermediate Similarity	NPD7640	Approved
0.7526	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.7474	Intermediate Similarity	NPD5695	Phase 3
0.7474	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4202	Approved
0.7423	Intermediate Similarity	NPD7638	Approved
0.7423	Intermediate Similarity	NPD5696	Approved
0.7416	Intermediate Similarity	NPD5362	Discontinued
0.7381	Intermediate Similarity	NPD6924	Approved
0.7381	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6926	Approved
0.7363	Intermediate Similarity	NPD4690	Approved
0.7363	Intermediate Similarity	NPD5205	Approved
0.7363	Intermediate Similarity	NPD4693	Phase 3
0.7363	Intermediate Similarity	NPD4689	Approved
0.7363	Intermediate Similarity	NPD4138	Approved
0.7363	Intermediate Similarity	NPD4688	Approved
0.7356	Intermediate Similarity	NPD6929	Approved
0.7347	Intermediate Similarity	NPD6404	Discontinued
0.734	Intermediate Similarity	NPD8035	Phase 2
0.734	Intermediate Similarity	NPD7637	Suspended
0.734	Intermediate Similarity	NPD5284	Approved
0.734	Intermediate Similarity	NPD5281	Approved
0.734	Intermediate Similarity	NPD8034	Phase 2
0.7333	Intermediate Similarity	NPD3668	Phase 3
0.7327	Intermediate Similarity	NPD6402	Approved
0.7327	Intermediate Similarity	NPD7128	Approved
0.7327	Intermediate Similarity	NPD5739	Approved
0.7327	Intermediate Similarity	NPD6675	Approved
0.7312	Intermediate Similarity	NPD6904	Approved
0.7312	Intermediate Similarity	NPD6080	Approved
0.7312	Intermediate Similarity	NPD6673	Approved
0.7292	Intermediate Similarity	NPD4629	Approved
0.7292	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD6931	Approved
0.7273	Intermediate Similarity	NPD6930	Phase 2
0.7273	Intermediate Similarity	NPD7525	Registered
0.725	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3617	Approved
0.7216	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5221	Approved
0.7216	Intermediate Similarity	NPD4697	Phase 3
0.7216	Intermediate Similarity	NPD5222	Approved
0.7209	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6117	Approved
0.7209	Intermediate Similarity	NPD6933	Approved
0.7204	Intermediate Similarity	NPD5208	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.7191	Intermediate Similarity	NPD6902	Approved
0.7188	Intermediate Similarity	NPD6001	Approved
0.7188	Intermediate Similarity	NPD7748	Approved
0.7184	Intermediate Similarity	NPD7320	Approved
0.7184	Intermediate Similarity	NPD6881	Approved
0.7184	Intermediate Similarity	NPD6899	Approved
0.7174	Intermediate Similarity	NPD5690	Phase 2
0.7174	Intermediate Similarity	NPD4694	Approved
0.7174	Intermediate Similarity	NPD4623	Approved
0.7174	Intermediate Similarity	NPD5280	Approved
0.7174	Intermediate Similarity	NPD4519	Discontinued
0.7158	Intermediate Similarity	NPD5693	Phase 1
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.7143	Intermediate Similarity	NPD5173	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7126	Intermediate Similarity	NPD6116	Phase 1
0.7126	Intermediate Similarity	NPD6925	Approved
0.7126	Intermediate Similarity	NPD5776	Phase 2
0.7115	Intermediate Similarity	NPD6373	Approved
0.7115	Intermediate Similarity	NPD6372	Approved
0.7111	Intermediate Similarity	NPD4269	Approved
0.7111	Intermediate Similarity	NPD4270	Approved
0.7108	Intermediate Similarity	NPD6922	Approved
0.7108	Intermediate Similarity	NPD6923	Approved
0.7087	Intermediate Similarity	NPD5697	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7059	Intermediate Similarity	NPD5141	Approved
0.7048	Intermediate Similarity	NPD7290	Approved
0.7048	Intermediate Similarity	NPD7102	Approved
0.7048	Intermediate Similarity	NPD6883	Approved
0.7045	Intermediate Similarity	NPD6118	Approved
0.7045	Intermediate Similarity	NPD6114	Approved
0.7045	Intermediate Similarity	NPD7145	Approved
0.7045	Intermediate Similarity	NPD6115	Approved
0.7045	Intermediate Similarity	NPD6697	Approved
0.7033	Intermediate Similarity	NPD5332	Approved
0.7033	Intermediate Similarity	NPD6695	Phase 3
0.7033	Intermediate Similarity	NPD5331	Approved
0.7024	Intermediate Similarity	NPD4747	Approved
0.7024	Intermediate Similarity	NPD4789	Approved
0.7024	Intermediate Similarity	NPD7143	Approved
0.7024	Intermediate Similarity	NPD7144	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD4790	Discontinued
0.7	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6617	Approved
0.6981	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6847	Approved
0.6981	Remote Similarity	NPD8130	Phase 1
0.6981	Remote Similarity	NPD6650	Approved
0.6981	Remote Similarity	NPD6869	Approved
0.6981	Remote Similarity	NPD6649	Approved
0.6979	Remote Similarity	NPD6050	Approved
0.6977	Remote Similarity	NPD4785	Approved
0.6977	Remote Similarity	NPD4784	Approved
0.697	Remote Similarity	NPD7902	Approved
0.6966	Remote Similarity	NPD4195	Approved
0.6957	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6951	Remote Similarity	NPD4224	Phase 2
0.6947	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6051	Approved
0.6941	Remote Similarity	NPD7150	Approved
0.6941	Remote Similarity	NPD6081	Approved
0.6941	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7152	Approved
0.6941	Remote Similarity	NPD7151	Approved
0.6941	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5223	Approved
0.6916	Remote Similarity	NPD8297	Approved
0.6916	Remote Similarity	NPD6882	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5133	Approved
0.6905	Remote Similarity	NPD4137	Phase 3
0.6897	Remote Similarity	NPD3702	Approved
0.6889	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD4822	Approved
0.6889	Remote Similarity	NPD4821	Approved
0.6889	Remote Similarity	NPD4819	Approved
0.6889	Remote Similarity	NPD7514	Phase 3
0.6889	Remote Similarity	NPD5368	Approved
0.6889	Remote Similarity	NPD4695	Discontinued
0.6889	Remote Similarity	NPD4820	Approved
0.6882	Remote Similarity	NPD5363	Approved
0.6882	Remote Similarity	NPD6893	Approved
0.6875	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD5207	Approved
0.6875	Remote Similarity	NPD5692	Phase 3
0.6863	Remote Similarity	NPD5224	Approved
0.6863	Remote Similarity	NPD7632	Discontinued
0.6863	Remote Similarity	NPD5225	Approved
0.6863	Remote Similarity	NPD4633	Approved
0.6863	Remote Similarity	NPD5226	Approved
0.6854	Remote Similarity	NPD4268	Approved
0.6854	Remote Similarity	NPD4271	Approved
0.6854	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7154	Phase 3
0.6824	Remote Similarity	NPD4245	Approved
0.6824	Remote Similarity	NPD4691	Approved
0.6824	Remote Similarity	NPD4244	Approved
0.6813	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD5786	Approved
0.6804	Remote Similarity	NPD5694	Approved
0.6804	Remote Similarity	NPD6411	Approved
0.6796	Remote Similarity	NPD4754	Approved
0.6796	Remote Similarity	NPD5174	Approved
0.6796	Remote Similarity	NPD5175	Approved
0.6786	Remote Similarity	NPD3621	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data