NPASS Compound

Structure

NPC247195 OpenBabel07101718272D 31 35 0 0 1 0 0 0 0 0999 V2000 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -0.0000 -2.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 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 -0.8660 -2.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 0.8660 -1.5000 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 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 -3.4641 -3.0000 0.0000 C 0 0 1 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 -2.5981 -1.5000 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 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 28 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 29 2 0 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 25 1 1 0 0 0 21 26 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 2 1 1 0 0 0 23 30 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 26 27 1 1 0 0 0 27 6 1 6 0 0 0 28 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.34
Volume:	473.796
LogP:	4.116
LogD:	3.583
LogS:	-4.779
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	5.023
Fsp3:	0.964
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:	-4.725
MDCK Permeability:	1.3305408174346667e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.737
Plasma Protein Binding (PPB):	90.40876770019531%
Volume Distribution (VD):	1.375
Pgp-substrate:	3.7799975872039795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.631

ADMET: Excretion

Clearance (CL):	12.26
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.298
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.859
Maximum Recommended Daily Dose:	0.635
Skin Sensitization:	0.808
Carcinogencity:	0.638
Eye Corrosion:	0.153
Eye Irritation:	0.031
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC247195

Natural Product ID:	NPC247195
*Common Name:**	28,29-Dihydroxyfriedelan-3-One
IUPAC Name:	(4R,4aS,6aS,6aS,6bR,8aR,11R,12aS,14aS,14bS)-8a,11-dihydroxy-4,4a,6a,6b,11,14a-hexamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
Synonyms:
Standard InCHIKey:	DPKBLLFCUGWECD-GTYQNAEWSA-N
Standard InCHI:	InChI=1S/C28H46O3/c1-18-19(29)7-8-20-24(18,3)10-9-21-25(20,4)12-13-27(6)22-17-23(2,30)11-15-28(22,31)16-14-26(21,27)5/h18,20-22,30-31H,7-17H2,1-6H3/t18-,20+,21-,22-,23+,24+,25-,26+,27-,28-/m0/s1
SMILES:	C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@](C)(CC[C@@]3(CC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467834
PubChem CID:	44566785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[515333]
NPT407	Cell Line	COLO 205	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[515333]

☑ 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 NPC247195 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	442
0.1-0.2	4378
0.2-0.3	16500
0.3-0.4	10108
0.4-0.5	5092
0.5-0.6	4259
0.6-0.7	1663
0.7-0.8	213
0.8-0.85	19
0.85-0.9	16
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC475977
0.9	High Similarity	NPC477229
0.9	High Similarity	NPC68426
0.9	High Similarity	NPC282905
0.8873	High Similarity	NPC159325
0.8873	High Similarity	NPC168511
0.875	High Similarity	NPC267753
0.8732	High Similarity	NPC81759
0.8696	High Similarity	NPC100917
0.8696	High Similarity	NPC469724
0.8696	High Similarity	NPC31187
0.8696	High Similarity	NPC180777
0.8696	High Similarity	NPC260319
0.8696	High Similarity	NPC281203
0.8696	High Similarity	NPC2568
0.8696	High Similarity	NPC103647
0.863	High Similarity	NPC108840
0.8611	High Similarity	NPC130011
0.8514	High Similarity	NPC112463
0.8429	Intermediate Similarity	NPC473225
0.84	Intermediate Similarity	NPC472608
0.8333	Intermediate Similarity	NPC290058
0.8312	Intermediate Similarity	NPC50658
0.8267	Intermediate Similarity	NPC23884
0.8261	Intermediate Similarity	NPC230047
0.8261	Intermediate Similarity	NPC19311
0.8243	Intermediate Similarity	NPC174964
0.8243	Intermediate Similarity	NPC195155
0.8243	Intermediate Similarity	NPC97534
0.8228	Intermediate Similarity	NPC34984
0.8228	Intermediate Similarity	NPC25037
0.8158	Intermediate Similarity	NPC26029
0.8158	Intermediate Similarity	NPC243594
0.8158	Intermediate Similarity	NPC31031
0.8133	Intermediate Similarity	NPC5767
0.8133	Intermediate Similarity	NPC475742
0.8108	Intermediate Similarity	NPC162164
0.8101	Intermediate Similarity	NPC269684
0.8077	Intermediate Similarity	NPC476071
0.8077	Intermediate Similarity	NPC271572
0.8077	Intermediate Similarity	NPC48756
0.8077	Intermediate Similarity	NPC474870
0.8077	Intermediate Similarity	NPC280781
0.8028	Intermediate Similarity	NPC41542
0.8026	Intermediate Similarity	NPC221420
0.8026	Intermediate Similarity	NPC475031
0.8	Intermediate Similarity	NPC105895
0.7973	Intermediate Similarity	NPC232112
0.7945	Intermediate Similarity	NPC108131
0.7867	Intermediate Similarity	NPC38426
0.7838	Intermediate Similarity	NPC58057
0.7838	Intermediate Similarity	NPC151018
0.7838	Intermediate Similarity	NPC320549
0.7838	Intermediate Similarity	NPC156277
0.7838	Intermediate Similarity	NPC89310
0.7808	Intermediate Similarity	NPC213178
0.7808	Intermediate Similarity	NPC6120
0.7808	Intermediate Similarity	NPC327728
0.7808	Intermediate Similarity	NPC131892
0.7808	Intermediate Similarity	NPC196197
0.7792	Intermediate Similarity	NPC143133
0.7792	Intermediate Similarity	NPC298168
0.7778	Intermediate Similarity	NPC472984
0.7763	Intermediate Similarity	NPC72444
0.7763	Intermediate Similarity	NPC273366
0.7733	Intermediate Similarity	NPC253805
0.7727	Intermediate Similarity	NPC307063
0.7714	Intermediate Similarity	NPC292419
0.7714	Intermediate Similarity	NPC290791
0.7683	Intermediate Similarity	NPC62572
0.7671	Intermediate Similarity	NPC474954
0.7671	Intermediate Similarity	NPC475893
0.7662	Intermediate Similarity	NPC472486
0.7662	Intermediate Similarity	NPC472487
0.7662	Intermediate Similarity	NPC104806
0.7647	Intermediate Similarity	NPC127798
0.7632	Intermediate Similarity	NPC254340
0.7595	Intermediate Similarity	NPC73013
0.7564	Intermediate Similarity	NPC317913
0.7564	Intermediate Similarity	NPC472746
0.7564	Intermediate Similarity	NPC207010
0.7561	Intermediate Similarity	NPC474996
0.7534	Intermediate Similarity	NPC204233
0.7532	Intermediate Similarity	NPC125767
0.7532	Intermediate Similarity	NPC212733
0.7532	Intermediate Similarity	NPC21220
0.7532	Intermediate Similarity	NPC159789
0.7531	Intermediate Similarity	NPC268040
0.7531	Intermediate Similarity	NPC61107
0.7531	Intermediate Similarity	NPC30583
0.7531	Intermediate Similarity	NPC289486
0.75	Intermediate Similarity	NPC260116
0.75	Intermediate Similarity	NPC475230
0.75	Intermediate Similarity	NPC80463
0.75	Intermediate Similarity	NPC261616
0.747	Intermediate Similarity	NPC133954
0.7439	Intermediate Similarity	NPC475726
0.7439	Intermediate Similarity	NPC472743
0.7439	Intermediate Similarity	NPC327451
0.7436	Intermediate Similarity	NPC4209
0.7432	Intermediate Similarity	NPC470956
0.7432	Intermediate Similarity	NPC472741
0.7432	Intermediate Similarity	NPC469987
0.7407	Intermediate Similarity	NPC469745
0.7407	Intermediate Similarity	NPC328264
0.7407	Intermediate Similarity	NPC473217
0.7403	Intermediate Similarity	NPC472854
0.7403	Intermediate Similarity	NPC280026
0.7403	Intermediate Similarity	NPC167702
0.7403	Intermediate Similarity	NPC133922
0.7397	Intermediate Similarity	NPC42060
0.7381	Intermediate Similarity	NPC74363
0.7381	Intermediate Similarity	NPC187545
0.7381	Intermediate Similarity	NPC213412
0.7381	Intermediate Similarity	NPC475862
0.7375	Intermediate Similarity	NPC320144
0.7349	Intermediate Similarity	NPC474482
0.7349	Intermediate Similarity	NPC219535
0.7349	Intermediate Similarity	NPC473299
0.7349	Intermediate Similarity	NPC50438
0.7349	Intermediate Similarity	NPC475745
0.7349	Intermediate Similarity	NPC237938
0.7333	Intermediate Similarity	NPC321732
0.7333	Intermediate Similarity	NPC474962
0.7333	Intermediate Similarity	NPC324607
0.7297	Intermediate Similarity	NPC48079
0.7294	Intermediate Similarity	NPC73064
0.7284	Intermediate Similarity	NPC18955
0.7273	Intermediate Similarity	NPC36310
0.7273	Intermediate Similarity	NPC472147
0.7273	Intermediate Similarity	NPC472148
0.7273	Intermediate Similarity	NPC310766
0.7262	Intermediate Similarity	NPC131350
0.7262	Intermediate Similarity	NPC292553
0.726	Intermediate Similarity	NPC469791
0.725	Intermediate Similarity	NPC80089
0.725	Intermediate Similarity	NPC171426
0.725	Intermediate Similarity	NPC185465
0.725	Intermediate Similarity	NPC324700
0.725	Intermediate Similarity	NPC224802
0.725	Intermediate Similarity	NPC34046
0.7246	Intermediate Similarity	NPC135438
0.7246	Intermediate Similarity	NPC236588
0.7241	Intermediate Similarity	NPC185529
0.7241	Intermediate Similarity	NPC50443
0.7241	Intermediate Similarity	NPC472146
0.7241	Intermediate Similarity	NPC18536
0.7237	Intermediate Similarity	NPC163020
0.7237	Intermediate Similarity	NPC476731
0.7209	Intermediate Similarity	NPC230387
0.72	Intermediate Similarity	NPC478228
0.7195	Intermediate Similarity	NPC267691
0.7195	Intermediate Similarity	NPC263272
0.7195	Intermediate Similarity	NPC58631
0.7195	Intermediate Similarity	NPC274050
0.7195	Intermediate Similarity	NPC162632
0.7195	Intermediate Similarity	NPC3915
0.7195	Intermediate Similarity	NPC12933
0.7191	Intermediate Similarity	NPC160413
0.7179	Intermediate Similarity	NPC255168
0.7179	Intermediate Similarity	NPC74639
0.7179	Intermediate Similarity	NPC96759
0.7176	Intermediate Similarity	NPC475276
0.7176	Intermediate Similarity	NPC477579
0.7176	Intermediate Similarity	NPC472738
0.7176	Intermediate Similarity	NPC476726
0.7176	Intermediate Similarity	NPC476727
0.7176	Intermediate Similarity	NPC72638
0.7176	Intermediate Similarity	NPC83242
0.7176	Intermediate Similarity	NPC235341
0.7176	Intermediate Similarity	NPC95594
0.7176	Intermediate Similarity	NPC471737
0.7162	Intermediate Similarity	NPC103734
0.7162	Intermediate Similarity	NPC84562
0.7162	Intermediate Similarity	NPC268736
0.7162	Intermediate Similarity	NPC142712
0.7162	Intermediate Similarity	NPC477931
0.716	Intermediate Similarity	NPC201459
0.716	Intermediate Similarity	NPC201276
0.716	Intermediate Similarity	NPC192744
0.716	Intermediate Similarity	NPC80891
0.7159	Intermediate Similarity	NPC105189
0.7159	Intermediate Similarity	NPC235704
0.7143	Intermediate Similarity	NPC74595
0.7143	Intermediate Similarity	NPC126642
0.7143	Intermediate Similarity	NPC171789
0.7143	Intermediate Similarity	NPC180834
0.7143	Intermediate Similarity	NPC251170
0.7143	Intermediate Similarity	NPC264665
0.7143	Intermediate Similarity	NPC478227
0.7143	Intermediate Similarity	NPC127094
0.7143	Intermediate Similarity	NPC472309
0.7143	Intermediate Similarity	NPC162685
0.7143	Intermediate Similarity	NPC473267
0.7143	Intermediate Similarity	NPC474233
0.7126	Intermediate Similarity	NPC25906
0.7126	Intermediate Similarity	NPC471459
0.7126	Intermediate Similarity	NPC290972
0.7126	Intermediate Similarity	NPC69627
0.7126	Intermediate Similarity	NPC67653

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 NPC247195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	561
0.1-0.2	4183
0.2-0.3	3179
0.3-0.4	755
0.4-0.5	235
0.5-0.6	195
0.6-0.7	31
0.7-0.8	11
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
0.8429	Intermediate Similarity	NPD5360	Phase 3
0.8429	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4758	Discontinued
0.7838	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4224	Phase 2
0.7564	Intermediate Similarity	NPD6116	Phase 1
0.7532	Intermediate Similarity	NPD3703	Phase 2
0.7468	Intermediate Similarity	NPD5364	Discontinued
0.7467	Intermediate Similarity	NPD4244	Approved
0.7467	Intermediate Similarity	NPD4789	Approved
0.7467	Intermediate Similarity	NPD4245	Approved
0.7436	Intermediate Similarity	NPD6117	Approved
0.7403	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6081	Approved
0.7333	Intermediate Similarity	NPD3698	Phase 2
0.726	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6115	Approved
0.725	Intermediate Similarity	NPD6697	Approved
0.725	Intermediate Similarity	NPD6114	Approved
0.725	Intermediate Similarity	NPD6118	Approved
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3671	Phase 1
0.6966	Remote Similarity	NPD7515	Phase 2
0.6813	Remote Similarity	NPD7748	Approved
0.6778	Remote Similarity	NPD8035	Phase 2
0.6778	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD7902	Approved
0.6709	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD3702	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4788	Approved
0.6452	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3618	Phase 1
0.6375	Remote Similarity	NPD4787	Phase 1
0.6374	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6353	Remote Similarity	NPD7645	Phase 2
0.6344	Remote Similarity	NPD4202	Approved
0.6338	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3667	Approved
0.6322	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD4223	Phase 3
0.6292	Remote Similarity	NPD5329	Approved
0.6237	Remote Similarity	NPD6079	Approved
0.6207	Remote Similarity	NPD4139	Approved
0.6207	Remote Similarity	NPD4692	Approved
0.618	Remote Similarity	NPD4197	Approved
0.6154	Remote Similarity	NPD3573	Approved
0.6092	Remote Similarity	NPD7525	Registered
0.6092	Remote Similarity	NPD4695	Discontinued
0.6082	Remote Similarity	NPD4755	Approved
0.6044	Remote Similarity	NPD4138	Approved
0.6044	Remote Similarity	NPD4693	Phase 3
0.6044	Remote Similarity	NPD5205	Approved
0.6044	Remote Similarity	NPD4689	Approved
0.6044	Remote Similarity	NPD4688	Approved
0.6044	Remote Similarity	NPD4623	Approved
0.6044	Remote Similarity	NPD4519	Discontinued
0.6044	Remote Similarity	NPD4690	Approved
0.604	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD3665	Phase 1
0.5979	Remote Similarity	NPD7614	Phase 1
0.596	Remote Similarity	NPD4700	Approved
0.596	Remote Similarity	NPD5285	Approved
0.596	Remote Similarity	NPD5286	Approved
0.596	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD6928	Phase 2
0.59	Remote Similarity	NPD5223	Approved
0.5882	Remote Similarity	NPD386	Approved
0.5882	Remote Similarity	NPD388	Approved
0.587	Remote Similarity	NPD5690	Phase 2
0.587	Remote Similarity	NPD4694	Approved
0.587	Remote Similarity	NPD5280	Approved
0.5865	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4753	Phase 2
0.5842	Remote Similarity	NPD5226	Approved
0.5842	Remote Similarity	NPD4633	Approved
0.5842	Remote Similarity	NPD5211	Phase 2
0.5842	Remote Similarity	NPD5225	Approved
0.5842	Remote Similarity	NPD5224	Approved
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD6920	Discontinued
0.5825	Remote Similarity	NPD6675	Approved
0.5824	Remote Similarity	NPD3668	Phase 3
0.5816	Remote Similarity	NPD4697	Phase 3
0.5816	Remote Similarity	NPD5221	Approved
0.5816	Remote Similarity	NPD5222	Approved
0.5816	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.58	Remote Similarity	NPD8418	Phase 2
0.5784	Remote Similarity	NPD5175	Approved
0.5784	Remote Similarity	NPD4754	Approved
0.5784	Remote Similarity	NPD5174	Approved
0.5758	Remote Similarity	NPD5173	Approved
0.575	Remote Similarity	NPD7341	Phase 2
0.5745	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5281	Approved
0.5729	Remote Similarity	NPD5284	Approved
0.5728	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5699	Remote Similarity	NPD6098	Approved
0.5676	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD4768	Approved
0.566	Remote Similarity	NPD6372	Approved
0.566	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD634	Phase 3
0.5619	Remote Similarity	NPD5697	Approved
0.5619	Remote Similarity	NPD5701	Approved
0.5618	Remote Similarity	NPD4195	Approved
0.5616	Remote Similarity	NPD3186	Phase 1
0.5607	Remote Similarity	NPD6883	Approved
0.5607	Remote Similarity	NPD7102	Approved
0.5607	Remote Similarity	NPD7290	Approved
0.56	Remote Similarity	NPD6084	Phase 2
0.56	Remote Similarity	NPD6083	Phase 2

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