NPASS Compound

Structure

NPC66344 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -6.5446 4.7859 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 4.3301 -2.5000 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 -4.2793 3.4190 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 -5.2574 3.6270 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 0.8660 0.5000 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 -5.5665 4.5780 0.0000 C 0 0 0 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 -2.6831 1.3090 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 5.3212 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 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2063 6.2722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9192 5.1132 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 7 2 0 0 0 0 3 21 1 0 0 0 0 4 27 1 0 0 0 0 6 34 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 20 2 1 1 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 6 0 0 0 23 27 1 6 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 31 2 0 0 0 0 25 34 1 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 27 28 1 6 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	6.171
LogD:	4.836
LogS:	-4.914
# Rotatable Bonds:	10
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	5.537
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:	-5.105
MDCK Permeability:	1.8267483028466813e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	96.59050750732422%
Volume Distribution (VD):	0.54
Pgp-substrate:	3.352348566055298%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.511
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.297
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.812
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	3.183
Half-life (T1/2):	0.37

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.696
Skin Sensitization:	0.951
Carcinogencity:	0.44
Eye Corrosion:	0.023
Eye Irritation:	0.037
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC66344

Natural Product ID:	NPC66344
*Common Name:**	Sinocalycanchinensin B
IUPAC Name:	n.a.
Synonyms:	Sinocalycanchinensin B
Standard InCHIKey:	JDMVZCVPHOWJJQ-RKLLWIJMSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-7-22-11-12-24-28(5)15-13-23(20(2)9-8-10-21(3)26(32)33)27(28,4)17-18-30(24)19-29(22,30)16-14-25(31)34-6/h7,10,20,22-24H,1,8-9,11-19H2,2-6H3,(H,32,33)/b21-10-/t20-,22-,23-,24+,27-,28+,29-,30+/m1/s1
SMILES:	C=C[C@@H]1CC[C@H]2[C@]3(C)CC[C@H]([C@H](C)CC/C=C(/C)C(=O)O)[C@@]3(C)CC[C@@]32C[C@]13CCC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774186
PubChem CID:	54584285
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33379	sinocalycanthus chinensis	Species	n.a.	n.a.	leaves	n.a.	n.a.	PMID[21493075]

☑ 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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	20.9	ug.mL-1	PMID[508374]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35.7	ug.mL-1	PMID[508374]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	17.6	ug.mL-1	PMID[508374]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	16.5	ug.mL-1	PMID[508374]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22.2	ug.mL-1	PMID[508374]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18.9	ug.mL-1	PMID[508374]

☑ 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 NPC66344 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	158
0.1-0.2	1026
0.2-0.3	4683
0.3-0.4	14362
0.4-0.5	8531
0.5-0.6	7224
0.6-0.7	5183
0.7-0.8	1388
0.8-0.85	104
0.85-0.9	22
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC236618
0.9639	High Similarity	NPC186975
0.9535	High Similarity	NPC470113
0.9432	High Similarity	NPC293052
0.9412	High Similarity	NPC117122
0.931	High Similarity	NPC476187
0.9186	High Similarity	NPC472870
0.9167	High Similarity	NPC19849
0.9167	High Similarity	NPC472864
0.9167	High Similarity	NPC164577
0.9091	High Similarity	NPC474018
0.9091	High Similarity	NPC473986
0.907	High Similarity	NPC128644
0.9059	High Similarity	NPC283733
0.9048	High Similarity	NPC97913
0.9	High Similarity	NPC476174
0.8953	High Similarity	NPC472869
0.8941	High Similarity	NPC194937
0.8941	High Similarity	NPC472865
0.8941	High Similarity	NPC476038
0.8913	High Similarity	NPC98868
0.8901	High Similarity	NPC29152
0.8864	High Similarity	NPC262043
0.8837	High Similarity	NPC269638
0.8804	High Similarity	NPC156546
0.8795	High Similarity	NPC158846
0.8778	High Similarity	NPC472871
0.8764	High Similarity	NPC472866
0.8721	High Similarity	NPC248758
0.8675	High Similarity	NPC198240
0.8636	High Similarity	NPC136948
0.8621	High Similarity	NPC29447
0.8621	High Similarity	NPC60350
0.8588	High Similarity	NPC40228
0.8587	High Similarity	NPC33473
0.8554	High Similarity	NPC61952
0.8526	High Similarity	NPC118174
0.8506	High Similarity	NPC178025
0.8506	High Similarity	NPC16287
0.8506	High Similarity	NPC181743
0.8495	Intermediate Similarity	NPC301534
0.8495	Intermediate Similarity	NPC250757
0.8478	Intermediate Similarity	NPC124207
0.8462	Intermediate Similarity	NPC204341
0.8444	Intermediate Similarity	NPC174342
0.8427	Intermediate Similarity	NPC476293
0.8421	Intermediate Similarity	NPC470074
0.8409	Intermediate Similarity	NPC65661
0.8391	Intermediate Similarity	NPC3856
0.8391	Intermediate Similarity	NPC279639
0.8391	Intermediate Similarity	NPC167103
0.8372	Intermediate Similarity	NPC477372
0.837	Intermediate Similarity	NPC476304
0.8352	Intermediate Similarity	NPC477147
0.8352	Intermediate Similarity	NPC477149
0.8351	Intermediate Similarity	NPC476237
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC476223
0.8316	Intermediate Similarity	NPC108368
0.8316	Intermediate Similarity	NPC57079
0.8298	Intermediate Similarity	NPC472941
0.8298	Intermediate Similarity	NPC456
0.8295	Intermediate Similarity	NPC165064
0.828	Intermediate Similarity	NPC476186
0.8276	Intermediate Similarity	NPC469805
0.8276	Intermediate Similarity	NPC469806
0.8276	Intermediate Similarity	NPC469804
0.8276	Intermediate Similarity	NPC469799
0.8276	Intermediate Similarity	NPC472239
0.8276	Intermediate Similarity	NPC100297
0.8276	Intermediate Similarity	NPC320514
0.8261	Intermediate Similarity	NPC74296
0.8261	Intermediate Similarity	NPC23217
0.8261	Intermediate Similarity	NPC110923
0.8242	Intermediate Similarity	NPC128496
0.8242	Intermediate Similarity	NPC310236
0.8242	Intermediate Similarity	NPC214387
0.8235	Intermediate Similarity	NPC239098
0.8229	Intermediate Similarity	NPC476274
0.8229	Intermediate Similarity	NPC266955
0.8229	Intermediate Similarity	NPC476303
0.8211	Intermediate Similarity	NPC107243
0.8211	Intermediate Similarity	NPC253826
0.8202	Intermediate Similarity	NPC86316
0.8202	Intermediate Similarity	NPC106416
0.8191	Intermediate Similarity	NPC171395
0.8191	Intermediate Similarity	NPC84383
0.8182	Intermediate Similarity	NPC215893
0.8172	Intermediate Similarity	NPC38232
0.8172	Intermediate Similarity	NPC151722
0.8172	Intermediate Similarity	NPC474736
0.8163	Intermediate Similarity	NPC72151
0.8163	Intermediate Similarity	NPC176883
0.8161	Intermediate Similarity	NPC278459
0.8161	Intermediate Similarity	NPC14203
0.8161	Intermediate Similarity	NPC147066
0.8161	Intermediate Similarity	NPC229584
0.8144	Intermediate Similarity	NPC99411
0.8144	Intermediate Similarity	NPC115899
0.8144	Intermediate Similarity	NPC282524
0.814	Intermediate Similarity	NPC477371
0.8132	Intermediate Similarity	NPC193843
0.8132	Intermediate Similarity	NPC104560
0.8132	Intermediate Similarity	NPC249889
0.8125	Intermediate Similarity	NPC235464
0.8125	Intermediate Similarity	NPC197386
0.8125	Intermediate Similarity	NPC166745
0.8111	Intermediate Similarity	NPC475007
0.8111	Intermediate Similarity	NPC70661
0.8105	Intermediate Similarity	NPC195366
0.8105	Intermediate Similarity	NPC328371
0.8105	Intermediate Similarity	NPC114743
0.8095	Intermediate Similarity	NPC472327
0.8095	Intermediate Similarity	NPC476795
0.8085	Intermediate Similarity	NPC299100
0.8085	Intermediate Similarity	NPC8993
0.8081	Intermediate Similarity	NPC235889
0.8068	Intermediate Similarity	NPC133391
0.8068	Intermediate Similarity	NPC472867
0.8068	Intermediate Similarity	NPC296367
0.8068	Intermediate Similarity	NPC200513
0.8068	Intermediate Similarity	NPC142253
0.8068	Intermediate Similarity	NPC3511
0.8065	Intermediate Similarity	NPC475806
0.8065	Intermediate Similarity	NPC179517
0.8065	Intermediate Similarity	NPC473998
0.8065	Intermediate Similarity	NPC165904
0.8065	Intermediate Similarity	NPC477783
0.8061	Intermediate Similarity	NPC320447
0.8046	Intermediate Similarity	NPC469798
0.8046	Intermediate Similarity	NPC104545
0.8046	Intermediate Similarity	NPC469797
0.8043	Intermediate Similarity	NPC473999
0.8043	Intermediate Similarity	NPC262858
0.8043	Intermediate Similarity	NPC146554
0.8043	Intermediate Similarity	NPC36668
0.8043	Intermediate Similarity	NPC118011
0.8043	Intermediate Similarity	NPC474570
0.8043	Intermediate Similarity	NPC309603
0.8043	Intermediate Similarity	NPC472240
0.8043	Intermediate Similarity	NPC5509
0.8041	Intermediate Similarity	NPC241221
0.8041	Intermediate Similarity	NPC201406
0.8041	Intermediate Similarity	NPC287833
0.8041	Intermediate Similarity	NPC471041
0.8023	Intermediate Similarity	NPC59436
0.8023	Intermediate Similarity	NPC179028
0.8023	Intermediate Similarity	NPC321514
0.8023	Intermediate Similarity	NPC321690
0.8022	Intermediate Similarity	NPC96496
0.8022	Intermediate Similarity	NPC476409
0.8022	Intermediate Similarity	NPC167877
0.8022	Intermediate Similarity	NPC93778
0.8021	Intermediate Similarity	NPC476253
0.8021	Intermediate Similarity	NPC108078
0.8021	Intermediate Similarity	NPC57416
0.8021	Intermediate Similarity	NPC202705
0.8021	Intermediate Similarity	NPC475894
0.8	Intermediate Similarity	NPC189863
0.8	Intermediate Similarity	NPC8571
0.8	Intermediate Similarity	NPC180950
0.8	Intermediate Similarity	NPC174948
0.8	Intermediate Similarity	NPC173875
0.8	Intermediate Similarity	NPC20466
0.8	Intermediate Similarity	NPC318282
0.8	Intermediate Similarity	NPC142649
0.8	Intermediate Similarity	NPC246445
0.8	Intermediate Similarity	NPC471224
0.8	Intermediate Similarity	NPC469995
0.8	Intermediate Similarity	NPC181265
0.798	Intermediate Similarity	NPC112009
0.798	Intermediate Similarity	NPC180204
0.7979	Intermediate Similarity	NPC472303
0.7979	Intermediate Similarity	NPC476416
0.7978	Intermediate Similarity	NPC477373
0.7978	Intermediate Similarity	NPC310470
0.7978	Intermediate Similarity	NPC472740
0.7978	Intermediate Similarity	NPC470015
0.7978	Intermediate Similarity	NPC474976
0.7978	Intermediate Similarity	NPC49019
0.7978	Intermediate Similarity	NPC168188
0.7978	Intermediate Similarity	NPC474790
0.7959	Intermediate Similarity	NPC472924
0.7957	Intermediate Similarity	NPC474842
0.7957	Intermediate Similarity	NPC48010
0.7957	Intermediate Similarity	NPC477782
0.7957	Intermediate Similarity	NPC51486
0.7957	Intermediate Similarity	NPC475965
0.7957	Intermediate Similarity	NPC476437
0.7957	Intermediate Similarity	NPC471896
0.7957	Intermediate Similarity	NPC476369
0.7955	Intermediate Similarity	NPC201912
0.7955	Intermediate Similarity	NPC90055
0.7955	Intermediate Similarity	NPC38350
0.7938	Intermediate Similarity	NPC252295
0.7935	Intermediate Similarity	NPC48107
0.7931	Intermediate Similarity	NPC274996
0.7931	Intermediate Similarity	NPC327674
0.7931	Intermediate Similarity	NPC196827

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 NPC66344 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	1282
0.2-0.3	3812
0.3-0.4	2692
0.4-0.5	740
0.5-0.6	189
0.6-0.7	187
0.7-0.8	111
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
0.8068	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5737	Approved
0.7935	Intermediate Similarity	NPD6672	Approved
0.7835	Intermediate Similarity	NPD6084	Phase 2
0.7835	Intermediate Similarity	NPD6083	Phase 2
0.7812	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7717	Intermediate Similarity	NPD7521	Approved
0.7717	Intermediate Similarity	NPD7334	Approved
0.7717	Intermediate Similarity	NPD7146	Approved
0.7717	Intermediate Similarity	NPD6409	Approved
0.7717	Intermediate Similarity	NPD6684	Approved
0.7717	Intermediate Similarity	NPD5330	Approved
0.7684	Intermediate Similarity	NPD5284	Approved
0.7684	Intermediate Similarity	NPD6079	Approved
0.7684	Intermediate Similarity	NPD5281	Approved
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.7677	Intermediate Similarity	NPD6404	Discontinued
0.7667	Intermediate Similarity	NPD4221	Approved
0.7667	Intermediate Similarity	NPD4223	Phase 3
0.766	Intermediate Similarity	NPD6080	Approved
0.766	Intermediate Similarity	NPD6904	Approved
0.766	Intermediate Similarity	NPD6673	Approved
0.7629	Intermediate Similarity	NPD5695	Phase 3
0.7614	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5329	Approved
0.7593	Intermediate Similarity	NPD7115	Discovery
0.7576	Intermediate Similarity	NPD7638	Approved
0.7576	Intermediate Similarity	NPD5696	Approved
0.7553	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6903	Approved
0.7527	Intermediate Similarity	NPD4623	Approved
0.7527	Intermediate Similarity	NPD5690	Phase 2
0.7527	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD5693	Phase 1
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.7474	Intermediate Similarity	NPD4753	Phase 2
0.7474	Intermediate Similarity	NPD5328	Approved
0.7449	Intermediate Similarity	NPD4629	Approved
0.7449	Intermediate Similarity	NPD5210	Approved
0.7404	Intermediate Similarity	NPD5697	Approved
0.7396	Intermediate Similarity	NPD5785	Approved
0.7391	Intermediate Similarity	NPD5362	Discontinued
0.7374	Intermediate Similarity	NPD5221	Approved
0.7374	Intermediate Similarity	NPD5222	Approved
0.7374	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5208	Approved
0.7358	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7102	Approved
0.7358	Intermediate Similarity	NPD7290	Approved
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.7347	Intermediate Similarity	NPD6001	Approved
0.7347	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD3618	Phase 1
0.734	Intermediate Similarity	NPD4693	Phase 3
0.734	Intermediate Similarity	NPD6098	Approved
0.734	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4138	Approved
0.734	Intermediate Similarity	NPD4689	Approved
0.734	Intermediate Similarity	NPD4690	Approved
0.734	Intermediate Similarity	NPD5205	Approved
0.734	Intermediate Similarity	NPD4688	Approved
0.7333	Intermediate Similarity	NPD4195	Approved
0.7333	Intermediate Similarity	NPD6011	Approved
0.732	Intermediate Similarity	NPD7637	Suspended
0.732	Intermediate Similarity	NPD7515	Phase 2
0.732	Intermediate Similarity	NPD6050	Approved
0.732	Intermediate Similarity	NPD5694	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.73	Intermediate Similarity	NPD5173	Approved
0.729	Intermediate Similarity	NPD6869	Approved
0.729	Intermediate Similarity	NPD6847	Approved
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6617	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.729	Intermediate Similarity	NPD8130	Phase 1
0.7283	Intermediate Similarity	NPD3667	Approved
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7234	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5363	Approved
0.7222	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD3617	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.7216	Intermediate Similarity	NPD5207	Approved
0.7216	Intermediate Similarity	NPD5692	Phase 3
0.7212	Intermediate Similarity	NPD5141	Approved
0.7204	Intermediate Similarity	NPD4788	Approved
0.717	Intermediate Similarity	NPD7320	Approved
0.7158	Intermediate Similarity	NPD4694	Approved
0.7158	Intermediate Similarity	NPD5280	Approved
0.7158	Intermediate Similarity	NPD5279	Phase 3
0.7157	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD5286	Approved
0.7157	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7129	Intermediate Similarity	NPD7902	Approved
0.7113	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.7087	Intermediate Similarity	NPD5223	Approved
0.7083	Intermediate Similarity	NPD3573	Approved
0.7075	Intermediate Similarity	NPD5701	Approved
0.7071	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD4225	Approved
0.7053	Intermediate Similarity	NPD1694	Approved
0.703	Intermediate Similarity	NPD4697	Phase 3
0.7027	Intermediate Similarity	NPD6868	Approved
0.7019	Intermediate Similarity	NPD5225	Approved
0.7019	Intermediate Similarity	NPD5226	Approved
0.7019	Intermediate Similarity	NPD4633	Approved
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7019	Intermediate Similarity	NPD5224	Approved
0.7011	Intermediate Similarity	NPD4691	Approved
0.7011	Intermediate Similarity	NPD4747	Approved
0.7009	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6972	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4058	Approved
0.6961	Remote Similarity	NPD5959	Approved
0.6961	Remote Similarity	NPD4755	Approved
0.6952	Remote Similarity	NPD5174	Approved
0.6952	Remote Similarity	NPD5175	Approved
0.6947	Remote Similarity	NPD3668	Phase 3
0.6939	Remote Similarity	NPD6051	Approved
0.6916	Remote Similarity	NPD6614	Approved
0.6915	Remote Similarity	NPD4270	Approved
0.6915	Remote Similarity	NPD4269	Approved
0.6903	Remote Similarity	NPD6335	Approved
0.69	Remote Similarity	NPD5133	Approved
0.6897	Remote Similarity	NPD7604	Phase 2
0.6897	Remote Similarity	NPD4137	Phase 3
0.6863	Remote Similarity	NPD7614	Phase 1
0.6857	Remote Similarity	NPD5091	Approved
0.6842	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD7101	Approved
0.6842	Remote Similarity	NPD5331	Approved
0.6842	Remote Similarity	NPD7154	Phase 3
0.6842	Remote Similarity	NPD5332	Approved
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6827	Remote Similarity	NPD4700	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.6814	Remote Similarity	NPD6009	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.6809	Remote Similarity	NPD6902	Approved
0.6809	Remote Similarity	NPD4790	Discontinued
0.6804	Remote Similarity	NPD5786	Approved
0.6792	Remote Similarity	NPD6052	Approved
0.6778	Remote Similarity	NPD4687	Approved
0.6778	Remote Similarity	NPD4784	Approved
0.6778	Remote Similarity	NPD4785	Approved
0.6778	Remote Similarity	NPD5733	Approved
0.6765	Remote Similarity	NPD5654	Approved
0.6759	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6742	Remote Similarity	NPD6081	Approved
0.6742	Remote Similarity	NPD4243	Approved
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6726	Remote Similarity	NPD6274	Approved
0.6703	Remote Similarity	NPD7339	Approved
0.6703	Remote Similarity	NPD8039	Approved
0.6703	Remote Similarity	NPD6942	Approved
0.6702	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4821	Approved
0.6702	Remote Similarity	NPD4252	Approved
0.6702	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD7525	Registered
0.6702	Remote Similarity	NPD4822	Approved
0.67	Remote Similarity	NPD4096	Approved
0.6699	Remote Similarity	NPD7732	Phase 3
0.6697	Remote Similarity	NPD5168	Approved
0.6697	Remote Similarity	NPD4730	Approved
0.6697	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6638	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD4754	Approved
0.6634	Remote Similarity	NPD6411	Approved
0.6632	Remote Similarity	NPD4139	Approved
0.6632	Remote Similarity	NPD5369	Approved
0.6632	Remote Similarity	NPD4692	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