NPASS Compound

Structure

NPC472733 OpenBabel07101718332D 36 38 0 0 1 0 0 0 0 0999 V2000 3.7461 1.2911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9067 0.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8206 -4.2642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1195 2.5043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 2.9669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1776 0.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3238 0.5394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 -2.3306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6970 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 -0.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3213 -0.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6413 -2.8428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6413 -1.8952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7360 -0.7191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9774 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9914 0.3758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8206 -3.3166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0405 2.2810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8206 -1.4214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3015 -0.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4497 -0.4764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3076 1.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6980 0.2153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3561 -0.9246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8206 -0.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3946 -0.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8206 -1.4214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8206 -0.4738 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 2.2285 1.1486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 1.1523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4619 0.4738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9284 -1.1885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0657 -1.0977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 28 1 0 0 0 0 8 28 1 0 0 0 0 10 30 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 21 1 0 0 0 0 15 30 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 20 24 1 0 0 0 0 21 30 1 1 0 0 0 22 25 1 0 0 0 0 22 26 2 0 0 0 0 23 28 1 6 0 0 0 23 36 1 0 0 0 0 24 32 2 0 0 0 0 25 31 1 0 0 0 0 25 33 2 0 0 0 0 26 29 1 0 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 31 1 0 0 0 0 27 34 2 0 0 0 0 28 35 1 0 0 0 0 29 9 1 1 0 0 0 30 31 1 6 0 0 0 31 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.33
Volume:	547.195
LogP:	6.371
LogD:	5.338
LogS:	-5.076
# Rotatable Bonds:	8
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	5.893
Fsp3:	0.71
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.02
MDCK Permeability:	1.686918767518364e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	92.17962646484375%
Volume Distribution (VD):	1.842
Pgp-substrate:	5.544941425323486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.862
CYP3A4-substrate:	0.932

ADMET: Excretion

Clearance (CL):	10.499
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.842
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.019
Carcinogencity:	0.712
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC472733

Natural Product ID:	NPC472733
*Common Name:**	XSFFQFMTHMLFBL-PBZDJEQUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XSFFQFMTHMLFBL-PBZDJEQUSA-N
Standard InCHI:	InChI=1S/C31H46O5/c1-18(2)12-11-15-30(10)21(14-13-19(3)4)17-29(9)26-22(16-23(36-26)28(7,8)35)25(33)31(30,27(29)34)24(32)20(5)6/h12-13,20-21,23,35H,11,14-17H2,1-10H3/t21-,23-,29+,30+,31-/m0/s1
SMILES:	CC(C)C(=O)C12C(=O)C3=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)C)OC(C3)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581917
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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
NPO32997	Hypericum monogynum	Species	Hypericaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[25924023]
NPO32997	Hypericum monogynum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27525351]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9500.0	nM	PMID[487397]

☑ 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 NPC472733 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	187
0.1-0.2	1204
0.2-0.3	4427
0.3-0.4	8892
0.4-0.5	13742
0.5-0.6	7629
0.6-0.7	5623
0.7-0.8	936
0.8-0.85	14
0.85-0.9	10
0.9-0.95	17
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472734
0.9889	High Similarity	NPC472731
0.9889	High Similarity	NPC472732
0.978	High Similarity	NPC177680
0.978	High Similarity	NPC472730
0.978	High Similarity	NPC153776
0.978	High Similarity	NPC472729
0.9674	High Similarity	NPC472727
0.9674	High Similarity	NPC472728
0.9457	High Similarity	NPC27105
0.9355	High Similarity	NPC99657
0.9355	High Similarity	NPC472687
0.9355	High Similarity	NPC471331
0.9355	High Similarity	NPC203388
0.9355	High Similarity	NPC471330
0.898	High Similarity	NPC471333
0.898	High Similarity	NPC471332
0.8936	High Similarity	NPC21681
0.8936	High Similarity	NPC472675
0.8842	High Similarity	NPC239895
0.8723	High Similarity	NPC469819
0.8723	High Similarity	NPC114162
0.8681	High Similarity	NPC38885
0.8526	High Similarity	NPC477241
0.8351	Intermediate Similarity	NPC93271
0.8351	Intermediate Similarity	NPC135576
0.8317	Intermediate Similarity	NPC13385
0.8222	Intermediate Similarity	NPC472684
0.8222	Intermediate Similarity	NPC44963
0.8131	Intermediate Similarity	NPC247069
0.81	Intermediate Similarity	NPC46761
0.81	Intermediate Similarity	NPC54705
0.8095	Intermediate Similarity	NPC239097
0.8061	Intermediate Similarity	NPC473170
0.8058	Intermediate Similarity	NPC478052
0.8039	Intermediate Similarity	NPC474330
0.8039	Intermediate Similarity	NPC474207
0.8022	Intermediate Similarity	NPC189237
0.8021	Intermediate Similarity	NPC472325
0.802	Intermediate Similarity	NPC475867
0.802	Intermediate Similarity	NPC270155
0.8019	Intermediate Similarity	NPC324683
0.8	Intermediate Similarity	NPC470257
0.7961	Intermediate Similarity	NPC40170
0.7959	Intermediate Similarity	NPC473172
0.7941	Intermediate Similarity	NPC473163
0.7941	Intermediate Similarity	NPC163249
0.7935	Intermediate Similarity	NPC212083
0.7889	Intermediate Similarity	NPC478247
0.7889	Intermediate Similarity	NPC478246
0.7872	Intermediate Similarity	NPC79573
0.7864	Intermediate Similarity	NPC264048
0.7857	Intermediate Similarity	NPC61275
0.7857	Intermediate Similarity	NPC474807
0.785	Intermediate Similarity	NPC474229
0.7835	Intermediate Similarity	NPC469464
0.7812	Intermediate Similarity	NPC143025
0.781	Intermediate Similarity	NPC58370
0.781	Intermediate Similarity	NPC43285
0.78	Intermediate Similarity	NPC473164
0.78	Intermediate Similarity	NPC8803
0.7789	Intermediate Similarity	NPC470345
0.7788	Intermediate Similarity	NPC255309
0.7778	Intermediate Similarity	NPC67831
0.7778	Intermediate Similarity	NPC174051
0.7778	Intermediate Similarity	NPC472976
0.7778	Intermediate Similarity	NPC325946
0.7778	Intermediate Similarity	NPC472977
0.7778	Intermediate Similarity	NPC473162
0.7778	Intermediate Similarity	NPC196227
0.7767	Intermediate Similarity	NPC80781
0.7757	Intermediate Similarity	NPC37116
0.7757	Intermediate Similarity	NPC473627
0.7755	Intermediate Similarity	NPC19114
0.7755	Intermediate Similarity	NPC116726
0.7755	Intermediate Similarity	NPC146852
0.7755	Intermediate Similarity	NPC262870
0.7755	Intermediate Similarity	NPC475441
0.7745	Intermediate Similarity	NPC112167
0.7745	Intermediate Similarity	NPC316964
0.7732	Intermediate Similarity	NPC32830
0.7732	Intermediate Similarity	NPC472688
0.7732	Intermediate Similarity	NPC472676
0.7732	Intermediate Similarity	NPC477943
0.7723	Intermediate Similarity	NPC472689
0.7723	Intermediate Similarity	NPC473161
0.7723	Intermediate Similarity	NPC477267
0.7723	Intermediate Similarity	NPC53844
0.7723	Intermediate Similarity	NPC477268
0.7723	Intermediate Similarity	NPC472690
0.7717	Intermediate Similarity	NPC2482
0.7714	Intermediate Similarity	NPC32006
0.7714	Intermediate Similarity	NPC96377
0.7714	Intermediate Similarity	NPC292588
0.7714	Intermediate Similarity	NPC102352
0.7714	Intermediate Similarity	NPC85529
0.7708	Intermediate Similarity	NPC472324
0.7708	Intermediate Similarity	NPC90652
0.7685	Intermediate Similarity	NPC43775
0.7684	Intermediate Similarity	NPC6185
0.7684	Intermediate Similarity	NPC8518
0.7684	Intermediate Similarity	NPC241512
0.7684	Intermediate Similarity	NPC263997
0.7684	Intermediate Similarity	NPC469948
0.7684	Intermediate Similarity	NPC132228
0.767	Intermediate Similarity	NPC181645
0.767	Intermediate Similarity	NPC477871
0.767	Intermediate Similarity	NPC476213
0.767	Intermediate Similarity	NPC476134
0.767	Intermediate Similarity	NPC101067
0.767	Intermediate Similarity	NPC477870
0.767	Intermediate Similarity	NPC476246
0.7664	Intermediate Similarity	NPC87335
0.766	Intermediate Similarity	NPC476082
0.766	Intermediate Similarity	NPC64600
0.766	Intermediate Similarity	NPC278648
0.7653	Intermediate Similarity	NPC113393
0.7653	Intermediate Similarity	NPC166554
0.7653	Intermediate Similarity	NPC280592
0.7653	Intermediate Similarity	NPC253177
0.7653	Intermediate Similarity	NPC15059
0.7653	Intermediate Similarity	NPC213636
0.7647	Intermediate Similarity	NPC147954
0.7642	Intermediate Similarity	NPC3316
0.7642	Intermediate Similarity	NPC473169
0.7642	Intermediate Similarity	NPC144854
0.7634	Intermediate Similarity	NPC327002
0.7634	Intermediate Similarity	NPC116797
0.7629	Intermediate Similarity	NPC476708
0.7629	Intermediate Similarity	NPC470417
0.7629	Intermediate Similarity	NPC53911
0.7624	Intermediate Similarity	NPC471463
0.7619	Intermediate Similarity	NPC149124
0.7619	Intermediate Similarity	NPC146731
0.7619	Intermediate Similarity	NPC75531
0.7615	Intermediate Similarity	NPC269530
0.7611	Intermediate Similarity	NPC478051
0.7604	Intermediate Similarity	NPC474732
0.7604	Intermediate Similarity	NPC474733
0.7604	Intermediate Similarity	NPC474778
0.7604	Intermediate Similarity	NPC31564
0.7604	Intermediate Similarity	NPC220478
0.7604	Intermediate Similarity	NPC145879
0.7604	Intermediate Similarity	NPC473168
0.7604	Intermediate Similarity	NPC477479
0.7604	Intermediate Similarity	NPC477478
0.7604	Intermediate Similarity	NPC194417
0.76	Intermediate Similarity	NPC318332
0.7596	Intermediate Similarity	NPC473424
0.7596	Intermediate Similarity	NPC477915
0.7596	Intermediate Similarity	NPC476126
0.7596	Intermediate Similarity	NPC476235
0.7596	Intermediate Similarity	NPC70369
0.7596	Intermediate Similarity	NPC478176
0.7596	Intermediate Similarity	NPC473928
0.7593	Intermediate Similarity	NPC29133
0.7579	Intermediate Similarity	NPC214043
0.7579	Intermediate Similarity	NPC85774
0.7579	Intermediate Similarity	NPC473246
0.7576	Intermediate Similarity	NPC296114
0.7576	Intermediate Similarity	NPC248913
0.7576	Intermediate Similarity	NPC471329
0.7576	Intermediate Similarity	NPC303697
0.7576	Intermediate Similarity	NPC230623
0.7573	Intermediate Similarity	NPC110149
0.7573	Intermediate Similarity	NPC117685
0.7573	Intermediate Similarity	NPC476274
0.7573	Intermediate Similarity	NPC474720
0.757	Intermediate Similarity	NPC473288
0.757	Intermediate Similarity	NPC192813
0.757	Intermediate Similarity	NPC473482
0.757	Intermediate Similarity	NPC318363
0.757	Intermediate Similarity	NPC154608
0.757	Intermediate Similarity	NPC277017
0.757	Intermediate Similarity	NPC151393
0.757	Intermediate Similarity	NPC475418
0.7568	Intermediate Similarity	NPC270929
0.7568	Intermediate Similarity	NPC207217
0.7556	Intermediate Similarity	NPC114236
0.7551	Intermediate Similarity	NPC474700
0.7551	Intermediate Similarity	NPC5509
0.7551	Intermediate Similarity	NPC86319
0.7551	Intermediate Similarity	NPC186688
0.7551	Intermediate Similarity	NPC474570
0.7551	Intermediate Similarity	NPC1015
0.7551	Intermediate Similarity	NPC275740
0.7551	Intermediate Similarity	NPC31985
0.7549	Intermediate Similarity	NPC273269
0.7549	Intermediate Similarity	NPC20078
0.7549	Intermediate Similarity	NPC473574
0.7549	Intermediate Similarity	NPC474977
0.7549	Intermediate Similarity	NPC124246
0.7547	Intermediate Similarity	NPC149047
0.7545	Intermediate Similarity	NPC198539
0.7542	Intermediate Similarity	NPC294050
0.7542	Intermediate Similarity	NPC328997
0.7527	Intermediate Similarity	NPC472948
0.7526	Intermediate Similarity	NPC23622
0.7526	Intermediate Similarity	NPC58063
0.7526	Intermediate Similarity	NPC99909

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 NPC472733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1556
0.2-0.3	3827
0.3-0.4	2391
0.4-0.5	761
0.5-0.6	216
0.6-0.7	213
0.7-0.8	16
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
0.7551	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.7426	Intermediate Similarity	NPD5282	Discontinued
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.74	Intermediate Similarity	NPD6079	Approved
0.7396	Intermediate Similarity	NPD4786	Approved
0.7396	Intermediate Similarity	NPD3133	Approved
0.7396	Intermediate Similarity	NPD3665	Phase 1
0.7396	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3667	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.734	Intermediate Similarity	NPD4695	Discontinued
0.7282	Intermediate Similarity	NPD4697	Phase 3
0.7255	Intermediate Similarity	NPD7748	Approved
0.7245	Intermediate Similarity	NPD7334	Approved
0.7245	Intermediate Similarity	NPD6684	Approved
0.7245	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6409	Approved
0.7245	Intermediate Similarity	NPD5330	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD6402	Approved
0.7222	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD6675	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7212	Intermediate Similarity	NPD4755	Approved
0.7212	Intermediate Similarity	NPD7902	Approved
0.72	Intermediate Similarity	NPD4753	Phase 2
0.7188	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD4221	Approved
0.7184	Intermediate Similarity	NPD5695	Phase 3
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD6373	Approved
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7115	Intermediate Similarity	NPD5222	Approved
0.7115	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5221	Approved
0.71	Intermediate Similarity	NPD6903	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6899	Approved
0.7091	Intermediate Similarity	NPD7320	Approved
0.7091	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7071	Intermediate Similarity	NPD5279	Phase 3
0.7059	Intermediate Similarity	NPD7515	Phase 2
0.7054	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD5173	Approved
0.7041	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD4197	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6101	Approved
0.7019	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6319	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.7009	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD5697	Approved
0.699	Remote Similarity	NPD4202	Approved
0.6964	Remote Similarity	NPD7102	Approved
0.6964	Remote Similarity	NPD6883	Approved
0.6964	Remote Similarity	NPD7290	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD5224	Approved
0.6937	Remote Similarity	NPD6011	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.6903	Remote Similarity	NPD6847	Approved
0.6903	Remote Similarity	NPD8130	Phase 1
0.6903	Remote Similarity	NPD6617	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6869	Approved
0.69	Remote Similarity	NPD4689	Approved
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4694	Approved
0.69	Remote Similarity	NPD4693	Phase 3
0.69	Remote Similarity	NPD5205	Approved
0.69	Remote Similarity	NPD5690	Phase 2
0.69	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD4138	Approved
0.69	Remote Similarity	NPD4690	Approved
0.69	Remote Similarity	NPD4623	Approved
0.6893	Remote Similarity	NPD5284	Approved
0.6893	Remote Similarity	NPD5281	Approved
0.6891	Remote Similarity	NPD6370	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD4754	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6875	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD6012	Approved
0.6875	Remote Similarity	NPD6013	Approved
0.6863	Remote Similarity	NPD6673	Approved
0.6863	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6904	Approved
0.6863	Remote Similarity	NPD6080	Approved
0.6857	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7331	Phase 2
0.6842	Remote Similarity	NPD6882	Approved
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8328	Phase 3
0.6832	Remote Similarity	NPD3573	Approved
0.6827	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.6807	Remote Similarity	NPD6016	Approved
0.6807	Remote Similarity	NPD6015	Approved
0.6786	Remote Similarity	NPD6686	Approved
0.6777	Remote Similarity	NPD7492	Approved
0.6768	Remote Similarity	NPD4788	Approved
0.6757	Remote Similarity	NPD4768	Approved
0.6757	Remote Similarity	NPD4767	Approved
0.675	Remote Similarity	NPD5988	Approved
0.6742	Remote Similarity	NPD7341	Phase 2
0.6735	Remote Similarity	NPD5369	Approved
0.6731	Remote Similarity	NPD6050	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4729	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6635	Remote Similarity	NPD5785	Approved
0.6635	Remote Similarity	NPD5207	Approved
0.6635	Remote Similarity	NPD5692	Phase 3
0.6634	Remote Similarity	NPD1694	Approved
0.6613	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6033	Approved
0.661	Remote Similarity	NPD6009	Approved
0.6602	Remote Similarity	NPD5208	Approved
0.66	Remote Similarity	NPD6110	Phase 1
0.6579	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5693	Phase 1
0.6571	Remote Similarity	NPD5694	Approved
0.6569	Remote Similarity	NPD5786	Approved
0.6569	Remote Similarity	NPD6098	Approved
0.6562	Remote Similarity	NPD6933	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6557	Remote Similarity	NPD7604	Phase 2
0.6555	Remote Similarity	NPD6335	Approved
0.6531	Remote Similarity	NPD4195	Approved
0.6529	Remote Similarity	NPD5983	Phase 2
0.6525	Remote Similarity	NPD6274	Approved
0.6525	Remote Similarity	NPD6868	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5135	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5169	Approved
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5251	Approved
0.6522	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5250	Approved
0.6514	Remote Similarity	NPD7638	Approved
0.6505	Remote Similarity	NPD7524	Approved
0.65	Remote Similarity	NPD7101	Approved
0.65	Remote Similarity	NPD7100	Approved
0.6491	Remote Similarity	NPD5168	Approved
0.6476	Remote Similarity	NPD4096	Approved
0.6471	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD5363	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5127	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6465	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7339	Approved
0.6458	Remote Similarity	NPD6942	Approved
0.6455	Remote Similarity	NPD7640	Approved
0.6455	Remote Similarity	NPD7639	Approved
0.6452	Remote Similarity	NPD4137	Phase 3
0.6452	Remote Similarity	NPD6336	Discontinued
0.6452	Remote Similarity	NPD7507	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