NPASS Compound

Structure

NPC470425 OpenBabel07101719402D 33 38 0 0 1 0 0 0 0 0999 V2000 1.4859 1.1540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2066 2.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6549 2.5925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9693 0.1370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2188 -0.2490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7582 0.9555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2066 0.6370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5516 1.5925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1033 1.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1190 0.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1033 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4980 1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5516 -0.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2864 -0.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5255 0.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2066 1.9110 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7582 1.5925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6549 0.9555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5516 0.9555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6740 -0.3740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1959 1.5680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1564 1.2895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1278 0.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6549 1.5925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1033 0.6370 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3954 0.3185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.6370 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 3.6243 2.0925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0431 2.5390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0883 1.0387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3868 1.3340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 17 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 30 1 1 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 26 1 1 0 0 0 20 28 1 0 0 0 0 21 27 1 6 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 27 1 6 0 0 0 23 33 1 0 0 0 0 24 29 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 6 0 0 0 29 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.32
Volume:	488.689
LogP:	4.103
LogD:	4.134
LogS:	-4.96
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	6.865
Fsp3:	0.897
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:	-4.969
MDCK Permeability:	2.5317451218143106e-05
Pgp-inhibitor:	0.893
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.346

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.415
Plasma Protein Binding (PPB):	78.6199722290039%
Volume Distribution (VD):	0.502
Pgp-substrate:	15.926216125488281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.371
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	7.748
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.507
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.604
Carcinogencity:	0.291
Eye Corrosion:	0.005
Eye Irritation:	0.037
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC470425

Natural Product ID:	NPC470425
*Common Name:**	Glaucalactone
IUPAC Name:	n.a.
Synonyms:	glaucalactone
Standard InCHIKey:	WCRHKJYIDBGGKV-DVIAKVNHSA-N
Standard InCHI:	InChI=1S/C29H44O4/c1-16-15-21-27(5)11-13-28(6)20-9-10-25(3)17(2)18(30)7-8-19(25)26(20,4)12-14-29(21,28)24(32)33-23(27)22(16)31/h17-23,30-31H,1,7-15H2,2-6H3/t17-,18-,19+,20-,21+,22-,23-,25+,26-,27+,28+,29-/m0/s1
SMILES:	C=C1C[C@@H]2[C@@]3([C@H]([C@H]1O)OC(=O)[C@@]12CC[C@@]2([C@@H]([C@]1(CC3)C)CC[C@]1([C@H]2CC[C@@H]([C@@H]1C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035572
PubChem CID:	57408885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO13364	Caloncoba glauca	Species	Achariaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22360639]
NPO13364	Caloncoba glauca	Species	Achariaceae	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
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	<	50.0	%	PMID[468339]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	<	50.0	%	PMID[468339]
NPT1138	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	Inhibition	<	50.0	%	PMID[468339]
NPT4861	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Mus musculus	Inhibition	<	50.0	%	PMID[468339]

☑ 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 NPC470425 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	257
0.1-0.2	1763
0.2-0.3	5184
0.3-0.4	13183
0.4-0.5	10125
0.5-0.6	5697
0.6-0.7	4420
0.7-0.8	1812
0.8-0.85	241
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC187545
0.8812	High Similarity	NPC154906
0.8687	High Similarity	NPC225238
0.8646	High Similarity	NPC230151
0.8632	High Similarity	NPC87095
0.8526	High Similarity	NPC307335
0.8526	High Similarity	NPC74855
0.8526	High Similarity	NPC136313
0.8485	Intermediate Similarity	NPC54909
0.8485	Intermediate Similarity	NPC233012
0.8454	Intermediate Similarity	NPC256227
0.8454	Intermediate Similarity	NPC317573
0.8438	Intermediate Similarity	NPC296164
0.8438	Intermediate Similarity	NPC303863
0.8421	Intermediate Similarity	NPC84319
0.8421	Intermediate Similarity	NPC25299
0.8421	Intermediate Similarity	NPC52021
0.8421	Intermediate Similarity	NPC71074
0.8421	Intermediate Similarity	NPC300351
0.8421	Intermediate Similarity	NPC306541
0.8421	Intermediate Similarity	NPC235884
0.8421	Intermediate Similarity	NPC472149
0.8404	Intermediate Similarity	NPC220498
0.8367	Intermediate Similarity	NPC259788
0.8367	Intermediate Similarity	NPC189880
0.8367	Intermediate Similarity	NPC255589
0.8351	Intermediate Similarity	NPC96916
0.8333	Intermediate Similarity	NPC133579
0.8333	Intermediate Similarity	NPC275809
0.8333	Intermediate Similarity	NPC474806
0.8316	Intermediate Similarity	NPC474728
0.8316	Intermediate Similarity	NPC49320
0.8298	Intermediate Similarity	NPC16377
0.8283	Intermediate Similarity	NPC58942
0.8283	Intermediate Similarity	NPC260149
0.8265	Intermediate Similarity	NPC207922
0.8265	Intermediate Similarity	NPC73004
0.8265	Intermediate Similarity	NPC104568
0.8265	Intermediate Similarity	NPC158371
0.8265	Intermediate Similarity	NPC259733
0.8265	Intermediate Similarity	NPC204961
0.8265	Intermediate Similarity	NPC173744
0.8252	Intermediate Similarity	NPC301666
0.8247	Intermediate Similarity	NPC88116
0.8247	Intermediate Similarity	NPC32407
0.8247	Intermediate Similarity	NPC20235
0.8247	Intermediate Similarity	NPC231063
0.8247	Intermediate Similarity	NPC263548
0.8247	Intermediate Similarity	NPC145667
0.8247	Intermediate Similarity	NPC469982
0.8247	Intermediate Similarity	NPC282395
0.8247	Intermediate Similarity	NPC299996
0.8229	Intermediate Similarity	NPC470590
0.8229	Intermediate Similarity	NPC77099
0.8229	Intermediate Similarity	NPC60755
0.8229	Intermediate Similarity	NPC285184
0.8211	Intermediate Similarity	NPC198664
0.8211	Intermediate Similarity	NPC470588
0.8211	Intermediate Similarity	NPC274330
0.8211	Intermediate Similarity	NPC143232
0.8191	Intermediate Similarity	NPC33768
0.8182	Intermediate Similarity	NPC247139
0.8182	Intermediate Similarity	NPC43686
0.8182	Intermediate Similarity	NPC9613
0.8163	Intermediate Similarity	NPC198245
0.8163	Intermediate Similarity	NPC473240
0.8163	Intermediate Similarity	NPC32118
0.8144	Intermediate Similarity	NPC86368
0.8144	Intermediate Similarity	NPC291373
0.8125	Intermediate Similarity	NPC470589
0.8125	Intermediate Similarity	NPC111110
0.8125	Intermediate Similarity	NPC120840
0.8125	Intermediate Similarity	NPC126369
0.8125	Intermediate Similarity	NPC185529
0.8125	Intermediate Similarity	NPC472146
0.8125	Intermediate Similarity	NPC113989
0.8105	Intermediate Similarity	NPC474512
0.8105	Intermediate Similarity	NPC181225
0.8105	Intermediate Similarity	NPC290690
0.8105	Intermediate Similarity	NPC40552
0.8105	Intermediate Similarity	NPC246708
0.8105	Intermediate Similarity	NPC473242
0.8105	Intermediate Similarity	NPC470629
0.8105	Intermediate Similarity	NPC182797
0.8105	Intermediate Similarity	NPC4309
0.8105	Intermediate Similarity	NPC52169
0.8105	Intermediate Similarity	NPC17733
0.81	Intermediate Similarity	NPC29765
0.81	Intermediate Similarity	NPC475876
0.81	Intermediate Similarity	NPC111214
0.81	Intermediate Similarity	NPC188833
0.81	Intermediate Similarity	NPC271614
0.8095	Intermediate Similarity	NPC310546
0.8095	Intermediate Similarity	NPC472534
0.8095	Intermediate Similarity	NPC143706
0.8085	Intermediate Similarity	NPC2783
0.8085	Intermediate Similarity	NPC12774
0.8081	Intermediate Similarity	NPC201657
0.8081	Intermediate Similarity	NPC19376
0.8081	Intermediate Similarity	NPC307282
0.8081	Intermediate Similarity	NPC305464
0.8081	Intermediate Similarity	NPC327179
0.8081	Intermediate Similarity	NPC476327
0.8081	Intermediate Similarity	NPC25848
0.8081	Intermediate Similarity	NPC476318
0.8081	Intermediate Similarity	NPC116457
0.8065	Intermediate Similarity	NPC130966
0.8061	Intermediate Similarity	NPC474529
0.8061	Intermediate Similarity	NPC188102
0.8061	Intermediate Similarity	NPC277399
0.8061	Intermediate Similarity	NPC91010
0.8061	Intermediate Similarity	NPC240617
0.8058	Intermediate Similarity	NPC284865
0.8056	Intermediate Similarity	NPC475633
0.8041	Intermediate Similarity	NPC187722
0.8041	Intermediate Similarity	NPC198054
0.8021	Intermediate Similarity	NPC270768
0.8021	Intermediate Similarity	NPC130520
0.8021	Intermediate Similarity	NPC290972
0.8021	Intermediate Similarity	NPC61543
0.8021	Intermediate Similarity	NPC225585
0.8021	Intermediate Similarity	NPC293048
0.8021	Intermediate Similarity	NPC30522
0.8021	Intermediate Similarity	NPC474686
0.8021	Intermediate Similarity	NPC64872
0.8021	Intermediate Similarity	NPC25906
0.8021	Intermediate Similarity	NPC127689
0.8021	Intermediate Similarity	NPC59263
0.8021	Intermediate Similarity	NPC263393
0.8021	Intermediate Similarity	NPC234346
0.8021	Intermediate Similarity	NPC121798
0.802	Intermediate Similarity	NPC35239
0.802	Intermediate Similarity	NPC476195
0.802	Intermediate Similarity	NPC473176
0.8	Intermediate Similarity	NPC171203
0.8	Intermediate Similarity	NPC18064
0.8	Intermediate Similarity	NPC130577
0.8	Intermediate Similarity	NPC293564
0.8	Intermediate Similarity	NPC4643
0.8	Intermediate Similarity	NPC68160
0.8	Intermediate Similarity	NPC476932
0.8	Intermediate Similarity	NPC307426
0.8	Intermediate Similarity	NPC142415
0.8	Intermediate Similarity	NPC98442
0.8	Intermediate Similarity	NPC106112
0.8	Intermediate Similarity	NPC264005
0.8	Intermediate Similarity	NPC102683
0.8	Intermediate Similarity	NPC158347
0.8	Intermediate Similarity	NPC242468
0.8	Intermediate Similarity	NPC51700
0.8	Intermediate Similarity	NPC269360
0.8	Intermediate Similarity	NPC261935
0.8	Intermediate Similarity	NPC88716
0.7981	Intermediate Similarity	NPC80566
0.7981	Intermediate Similarity	NPC477877
0.798	Intermediate Similarity	NPC195715
0.798	Intermediate Similarity	NPC139570
0.798	Intermediate Similarity	NPC53565
0.798	Intermediate Similarity	NPC474727
0.7979	Intermediate Similarity	NPC264317
0.7979	Intermediate Similarity	NPC294438
0.7961	Intermediate Similarity	NPC277074
0.7961	Intermediate Similarity	NPC90177
0.7961	Intermediate Similarity	NPC209298
0.7959	Intermediate Similarity	NPC475061
0.7959	Intermediate Similarity	NPC158059
0.7959	Intermediate Similarity	NPC49776
0.7959	Intermediate Similarity	NPC214756
0.7959	Intermediate Similarity	NPC294263
0.7959	Intermediate Similarity	NPC272075
0.7959	Intermediate Similarity	NPC471902
0.7959	Intermediate Similarity	NPC202728
0.7959	Intermediate Similarity	NPC473690
0.7959	Intermediate Similarity	NPC63118
0.7959	Intermediate Similarity	NPC287118
0.7959	Intermediate Similarity	NPC244356
0.7959	Intermediate Similarity	NPC224060
0.7959	Intermediate Similarity	NPC474436
0.7959	Intermediate Similarity	NPC295643
0.7959	Intermediate Similarity	NPC229281
0.7959	Intermediate Similarity	NPC118519
0.7957	Intermediate Similarity	NPC471037
0.7944	Intermediate Similarity	NPC56025
0.7941	Intermediate Similarity	NPC256247
0.7941	Intermediate Similarity	NPC476132
0.7941	Intermediate Similarity	NPC252614
0.7938	Intermediate Similarity	NPC290614
0.7938	Intermediate Similarity	NPC291028
0.7938	Intermediate Similarity	NPC210037
0.7938	Intermediate Similarity	NPC120968
0.7938	Intermediate Similarity	NPC227467
0.7938	Intermediate Similarity	NPC18872
0.7938	Intermediate Similarity	NPC130278
0.7938	Intermediate Similarity	NPC477872
0.7938	Intermediate Similarity	NPC7260
0.7938	Intermediate Similarity	NPC273621
0.7925	Intermediate Similarity	NPC240125
0.7925	Intermediate Similarity	NPC91583
0.7925	Intermediate Similarity	NPC127853
0.7921	Intermediate Similarity	NPC174663

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 NPC470425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	2160
0.2-0.3	3791
0.3-0.4	1949
0.4-0.5	605
0.5-0.6	254
0.6-0.7	128
0.7-0.8	13
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
0.7979	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7748	Approved
0.7857	Intermediate Similarity	NPD8035	Phase 2
0.7857	Intermediate Similarity	NPD7515	Phase 2
0.7857	Intermediate Similarity	NPD8034	Phase 2
0.7647	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7900	Approved
0.7353	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8133	Approved
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8328	Phase 3
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7087	Intermediate Similarity	NPD6399	Phase 3
0.7075	Intermediate Similarity	NPD7638	Approved
0.7075	Intermediate Similarity	NPD4225	Approved
0.7021	Intermediate Similarity	NPD6117	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.6979	Remote Similarity	NPD7645	Phase 2
0.6961	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5328	Approved
0.6961	Remote Similarity	NPD6101	Approved
0.6947	Remote Similarity	NPD6116	Phase 1
0.6942	Remote Similarity	NPD7507	Approved
0.6931	Remote Similarity	NPD3573	Approved
0.693	Remote Similarity	NPD8297	Approved
0.6875	Remote Similarity	NPD6118	Approved
0.6875	Remote Similarity	NPD7320	Approved
0.6875	Remote Similarity	NPD6115	Approved
0.6875	Remote Similarity	NPD6114	Approved
0.6875	Remote Similarity	NPD6881	Approved
0.6875	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD6697	Approved
0.6827	Remote Similarity	NPD6079	Approved
0.6814	Remote Similarity	NPD6373	Approved
0.6814	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6372	Approved
0.6809	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD5701	Approved
0.6786	Remote Similarity	NPD5697	Approved
0.6774	Remote Similarity	NPD7319	Approved
0.6768	Remote Similarity	NPD3667	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6754	Remote Similarity	NPD7290	Approved
0.6754	Remote Similarity	NPD6883	Approved
0.6754	Remote Similarity	NPD7102	Approved
0.675	Remote Similarity	NPD6921	Approved
0.6727	Remote Similarity	NPD7632	Discontinued
0.6726	Remote Similarity	NPD6011	Approved
0.6726	Remote Similarity	NPD6686	Approved
0.6724	Remote Similarity	NPD4632	Approved
0.6699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6847	Approved
0.6696	Remote Similarity	NPD6617	Approved
0.6696	Remote Similarity	NPD6649	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6869	Approved
0.6696	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6638	Remote Similarity	NPD6882	Approved
0.6637	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5211	Phase 2
0.6574	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4697	Phase 3
0.6574	Remote Similarity	NPD5222	Approved
0.6574	Remote Similarity	NPD5221	Approved
0.6562	Remote Similarity	NPD3703	Phase 2
0.6535	Remote Similarity	NPD4788	Approved
0.6529	Remote Similarity	NPD6319	Approved
0.6514	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD6083	Phase 2
0.6514	Remote Similarity	NPD4755	Approved
0.6505	Remote Similarity	NPD7334	Approved
0.6505	Remote Similarity	NPD6409	Approved
0.6505	Remote Similarity	NPD5330	Approved
0.6505	Remote Similarity	NPD7146	Approved
0.6505	Remote Similarity	NPD7521	Approved
0.6505	Remote Similarity	NPD6684	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8033	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6471	Remote Similarity	NPD6868	Approved
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5141	Approved
0.646	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7516	Approved
0.6429	Remote Similarity	NPD7736	Approved
0.6421	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6009	Approved
0.6404	Remote Similarity	NPD6008	Approved
0.64	Remote Similarity	NPD7525	Registered
0.6396	Remote Similarity	NPD4700	Approved
0.6396	Remote Similarity	NPD4696	Approved
0.6396	Remote Similarity	NPD5286	Approved
0.6396	Remote Similarity	NPD5285	Approved
0.6393	Remote Similarity	NPD8294	Approved
0.6393	Remote Similarity	NPD8377	Approved
0.6392	Remote Similarity	NPD3702	Approved
0.6383	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5737	Approved
0.6381	Remote Similarity	NPD6672	Approved
0.6381	Remote Similarity	NPD6903	Approved
0.6371	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD7327	Approved
0.6355	Remote Similarity	NPD7983	Approved
0.6341	Remote Similarity	NPD8296	Approved
0.6341	Remote Similarity	NPD5983	Phase 2
0.6341	Remote Similarity	NPD8380	Approved
0.6341	Remote Similarity	NPD8335	Approved
0.6341	Remote Similarity	NPD8379	Approved
0.6341	Remote Similarity	NPD8378	Approved
0.6339	Remote Similarity	NPD5223	Approved
0.6333	Remote Similarity	NPD6274	Approved
0.632	Remote Similarity	NPD7492	Approved
0.6311	Remote Similarity	NPD7101	Approved
0.6311	Remote Similarity	NPD7100	Approved
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD3666	Approved
0.6311	Remote Similarity	NPD3668	Phase 3
0.6311	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD4202	Approved
0.6286	Remote Similarity	NPD7524	Approved
0.6283	Remote Similarity	NPD5225	Approved
0.6283	Remote Similarity	NPD5226	Approved
0.6283	Remote Similarity	NPD4633	Approved
0.6283	Remote Similarity	NPD5224	Approved
0.6281	Remote Similarity	NPD6317	Approved
0.6275	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7614	Phase 1
0.627	Remote Similarity	NPD6336	Discontinued
0.627	Remote Similarity	NPD6616	Approved
0.6262	Remote Similarity	NPD46	Approved
0.6262	Remote Similarity	NPD6698	Approved
0.626	Remote Similarity	NPD6054	Approved
0.626	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD5777	Approved
0.623	Remote Similarity	NPD6314	Approved
0.623	Remote Similarity	NPD6313	Approved
0.6228	Remote Similarity	NPD5174	Approved
0.6228	Remote Similarity	NPD5175	Approved
0.6228	Remote Similarity	NPD4754	Approved
0.622	Remote Similarity	NPD8293	Discontinued
0.622	Remote Similarity	NPD7078	Approved
0.621	Remote Similarity	NPD6909	Approved
0.621	Remote Similarity	NPD6908	Approved
0.6207	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7637	Suspended
0.6195	Remote Similarity	NPD5344	Discontinued
0.619	Remote Similarity	NPD6422	Discontinued
0.6186	Remote Similarity	NPD4634	Approved
0.6182	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5695	Phase 3
0.6161	Remote Similarity	NPD5696	Approved
0.616	Remote Similarity	NPD6370	Approved
0.6146	Remote Similarity	NPD4245	Approved
0.6146	Remote Similarity	NPD4244	Approved
0.6134	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7732	Phase 3
0.6121	Remote Similarity	NPD4767	Approved
0.6121	Remote Similarity	NPD4768	Approved
0.6082	Remote Similarity	NPD6081	Approved
0.608	Remote Similarity	NPD6016	Approved
0.608	Remote Similarity	NPD7503	Approved
0.608	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6015	Approved
0.6078	Remote Similarity	NPD4695	Discontinued
0.6064	Remote Similarity	NPD4224	Phase 2
0.6061	Remote Similarity	NPD7339	Approved
0.6061	Remote Similarity	NPD6942	Approved
0.6058	Remote Similarity	NPD5362	Discontinued
0.6058	Remote Similarity	NPD7154	Phase 3
0.6042	Remote Similarity	NPD3698	Phase 2
0.6042	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6098	Approved
0.6038	Remote Similarity	NPD5786	Approved
0.6032	Remote Similarity	NPD5988	Approved
0.6019	Remote Similarity	NPD6904	Approved
0.6019	Remote Similarity	NPD6673	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