NPASS Compound

Structure

NPC473268 OpenBabel07101718292D 24 25 0 0 1 0 0 0 0 0999 V2000 2.7390 3.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7571 2.0129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0290 0.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.2148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2673 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -0.3460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2673 0.7367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4957 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 0.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4554 2.6409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8435 2.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4957 2.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0345 1.8319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4554 1.0229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4957 -0.2862 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0345 0.2138 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 0.1866 -1.2372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 -0.6997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0432 1.8319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 16 14 1 1 0 0 0 17 24 1 0 0 0 0 18 20 1 1 0 0 0 18 21 1 0 0 0 0 19 3 1 6 0 0 0 19 22 1 0 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	364.615
LogP:	3.45
LogD:	3.103
LogS:	-4.118
# Rotatable Bonds:	1
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	5.948
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.508
MDCK Permeability:	1.4373616977536585e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.188
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.787

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.584
Plasma Protein Binding (PPB):	87.7863540649414%
Volume Distribution (VD):	1.198
Pgp-substrate:	3.7193167209625244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.712

ADMET: Excretion

Clearance (CL):	10.203
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.049
Carcinogencity:	0.578
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC473268

Natural Product ID:	NPC473268
*Common Name:**	Furanocembranoid 3
IUPAC Name:	(4S,5E,7S,10R,11S)-7,11-dimethyl-4-propan-2-yl-14-oxabicyclo[11.2.1]hexadeca-1(15),5,13(16)-triene-7,10,11-triol
Synonyms:	Furanocembranoid 3
Standard InCHIKey:	HJQCZCWDLYWBEP-KAFAMHJCSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-14(2)16-6-5-15-11-17(24-13-15)12-20(4,23)18(21)8-10-19(3,22)9-7-16/h7,9,11,13-14,16,18,21-23H,5-6,8,10,12H2,1-4H3/b9-7+/t16-,18-,19-,20+/m1/s1
SMILES:	CC([C@H]1/C=C/[C@@](C)(O)CC[C@@H](O)[C@@](Cc2cc(CC1)co2)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388838
PubChem CID:	44421679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic compounds

*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
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479328]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17341114]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16932	Croton oblongifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	5.7	ug.mL-1	PMID[518799]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	5.6	ug.mL-1	PMID[518799]
NPT27	Others	Unspecified		IC50	=	9.6	ug.mL-1	PMID[518799]
NPT27	Others	Unspecified		IC50	=	7.1	ug.mL-1	PMID[518799]
NPT27	Others	Unspecified		IC50	=	8.2	ug.mL-1	PMID[518799]

☑ 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 NPC473268 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	288
0.1-0.2	1144
0.2-0.3	3238
0.3-0.4	8067
0.4-0.5	11154
0.5-0.6	5465
0.6-0.7	9762
0.7-0.8	3468
0.8-0.85	100
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9466	High Similarity	NPC106247
0.8992	High Similarity	NPC118853
0.8768	High Similarity	NPC472376
0.8723	High Similarity	NPC254198
0.8705	High Similarity	NPC107571
0.8692	High Similarity	NPC263870
0.8676	High Similarity	NPC474426
0.8676	High Similarity	NPC474425
0.8676	High Similarity	NPC474407
0.8571	High Similarity	NPC474219
0.8571	High Similarity	NPC474378
0.8551	High Similarity	NPC159786
0.8542	High Similarity	NPC104924
0.8511	High Similarity	NPC282973
0.8489	Intermediate Similarity	NPC303217
0.8467	Intermediate Similarity	NPC471545
0.8467	Intermediate Similarity	NPC471544
0.8467	Intermediate Similarity	NPC97740
0.8467	Intermediate Similarity	NPC473344
0.8467	Intermediate Similarity	NPC473982
0.8462	Intermediate Similarity	NPC476946
0.8444	Intermediate Similarity	NPC474438
0.8444	Intermediate Similarity	NPC474279
0.8409	Intermediate Similarity	NPC473379
0.8409	Intermediate Similarity	NPC471549
0.8394	Intermediate Similarity	NPC17681
0.837	Intermediate Similarity	NPC471554
0.837	Intermediate Similarity	NPC471501
0.837	Intermediate Similarity	NPC476016
0.837	Intermediate Similarity	NPC473355
0.837	Intermediate Similarity	NPC474830
0.837	Intermediate Similarity	NPC471573
0.8358	Intermediate Similarity	NPC474829
0.8333	Intermediate Similarity	NPC79557
0.8333	Intermediate Similarity	NPC45358
0.8309	Intermediate Similarity	NPC329707
0.8298	Intermediate Similarity	NPC170604
0.8298	Intermediate Similarity	NPC215109
0.8296	Intermediate Similarity	NPC329922
0.8296	Intermediate Similarity	NPC329694
0.8296	Intermediate Similarity	NPC474260
0.8296	Intermediate Similarity	NPC81912
0.8289	Intermediate Similarity	NPC116639
0.8261	Intermediate Similarity	NPC136340
0.8247	Intermediate Similarity	NPC288602
0.8247	Intermediate Similarity	NPC88841
0.8224	Intermediate Similarity	NPC194499
0.8222	Intermediate Similarity	NPC71274
0.8222	Intermediate Similarity	NPC75557
0.8219	Intermediate Similarity	NPC195920
0.8195	Intermediate Similarity	NPC1848
0.8194	Intermediate Similarity	NPC261184
0.8182	Intermediate Similarity	NPC188649
0.8182	Intermediate Similarity	NPC474615
0.8182	Intermediate Similarity	NPC18986
0.8176	Intermediate Similarity	NPC61284
0.8176	Intermediate Similarity	NPC113428
0.817	Intermediate Similarity	NPC474611
0.8169	Intermediate Similarity	NPC186626
0.8169	Intermediate Similarity	NPC286130
0.8168	Intermediate Similarity	NPC312525
0.8168	Intermediate Similarity	NPC217180
0.8163	Intermediate Similarity	NPC475864
0.8153	Intermediate Similarity	NPC296558
0.8151	Intermediate Similarity	NPC218712
0.8151	Intermediate Similarity	NPC307346
0.8151	Intermediate Similarity	NPC267004
0.8151	Intermediate Similarity	NPC261733
0.8146	Intermediate Similarity	NPC114880
0.8141	Intermediate Similarity	NPC121995
0.8138	Intermediate Similarity	NPC52412
0.8121	Intermediate Similarity	NPC474270
0.8121	Intermediate Similarity	NPC211625
0.8121	Intermediate Similarity	NPC475904
0.8117	Intermediate Similarity	NPC287559
0.8108	Intermediate Similarity	NPC308799
0.8106	Intermediate Similarity	NPC187547
0.8106	Intermediate Similarity	NPC21831
0.8105	Intermediate Similarity	NPC88007
0.8095	Intermediate Similarity	NPC5676
0.8095	Intermediate Similarity	NPC469642
0.8082	Intermediate Similarity	NPC64568
0.8082	Intermediate Similarity	NPC110305
0.8079	Intermediate Similarity	NPC294511
0.8079	Intermediate Similarity	NPC121615
0.8074	Intermediate Similarity	NPC476351
0.8074	Intermediate Similarity	NPC475818
0.8069	Intermediate Similarity	NPC205765
0.8067	Intermediate Similarity	NPC212257
0.8065	Intermediate Similarity	NPC68848
0.8065	Intermediate Similarity	NPC49009
0.8058	Intermediate Similarity	NPC45947
0.8056	Intermediate Similarity	NPC98395
0.8056	Intermediate Similarity	NPC90953
0.8054	Intermediate Similarity	NPC471618
0.8054	Intermediate Similarity	NPC474220
0.8054	Intermediate Similarity	NPC474255
0.8042	Intermediate Similarity	NPC278832
0.8042	Intermediate Similarity	NPC64157
0.8041	Intermediate Similarity	NPC97904
0.8041	Intermediate Similarity	NPC30890
0.8039	Intermediate Similarity	NPC41880
0.8039	Intermediate Similarity	NPC474542
0.8039	Intermediate Similarity	NPC469485
0.803	Intermediate Similarity	NPC208906
0.803	Intermediate Similarity	NPC144745
0.8029	Intermediate Similarity	NPC216810
0.8028	Intermediate Similarity	NPC158525
0.8028	Intermediate Similarity	NPC476947
0.8027	Intermediate Similarity	NPC137295
0.8027	Intermediate Similarity	NPC130206
0.8026	Intermediate Similarity	NPC275878
0.8015	Intermediate Similarity	NPC205523
0.8015	Intermediate Similarity	NPC243269
0.8014	Intermediate Similarity	NPC263337
0.8014	Intermediate Similarity	NPC214097
0.8014	Intermediate Similarity	NPC475519
0.8013	Intermediate Similarity	NPC283209
0.8013	Intermediate Similarity	NPC14822
0.8	Intermediate Similarity	NPC67003
0.8	Intermediate Similarity	NPC90296
0.8	Intermediate Similarity	NPC470998
0.8	Intermediate Similarity	NPC476350
0.8	Intermediate Similarity	NPC201370
0.8	Intermediate Similarity	NPC477402
0.8	Intermediate Similarity	NPC283284
0.8	Intermediate Similarity	NPC473983
0.8	Intermediate Similarity	NPC477645
0.8	Intermediate Similarity	NPC476349
0.8	Intermediate Similarity	NPC289911
0.8	Intermediate Similarity	NPC477967
0.7987	Intermediate Similarity	NPC250228
0.7987	Intermediate Similarity	NPC195954
0.7987	Intermediate Similarity	NPC173544
0.7987	Intermediate Similarity	NPC304692
0.7974	Intermediate Similarity	NPC264943
0.7974	Intermediate Similarity	NPC158261
0.7974	Intermediate Similarity	NPC42458
0.7973	Intermediate Similarity	NPC37488
0.7972	Intermediate Similarity	NPC46896
0.7971	Intermediate Similarity	NPC137570
0.7971	Intermediate Similarity	NPC290955
0.7961	Intermediate Similarity	NPC472423
0.7961	Intermediate Similarity	NPC474744
0.7961	Intermediate Similarity	NPC474772
0.7961	Intermediate Similarity	NPC44577
0.7959	Intermediate Similarity	NPC243577
0.7958	Intermediate Similarity	NPC200718
0.7956	Intermediate Similarity	NPC473885
0.7956	Intermediate Similarity	NPC471559
0.7956	Intermediate Similarity	NPC471074
0.7955	Intermediate Similarity	NPC45536
0.7955	Intermediate Similarity	NPC474987
0.7949	Intermediate Similarity	NPC303210
0.7949	Intermediate Similarity	NPC95472
0.7949	Intermediate Similarity	NPC79571
0.7949	Intermediate Similarity	NPC169
0.7949	Intermediate Similarity	NPC239270
0.7947	Intermediate Similarity	NPC228842
0.7945	Intermediate Similarity	NPC477535
0.7945	Intermediate Similarity	NPC477537
0.7945	Intermediate Similarity	NPC248795
0.7935	Intermediate Similarity	NPC296957
0.7935	Intermediate Similarity	NPC260902
0.7935	Intermediate Similarity	NPC269495
0.7935	Intermediate Similarity	NPC140952
0.7935	Intermediate Similarity	NPC472779
0.7933	Intermediate Similarity	NPC469425
0.7926	Intermediate Similarity	NPC474136
0.7922	Intermediate Similarity	NPC104736
0.7922	Intermediate Similarity	NPC180901
0.7922	Intermediate Similarity	NPC300757
0.7914	Intermediate Similarity	NPC279877
0.7911	Intermediate Similarity	NPC475779
0.791	Intermediate Similarity	NPC473969
0.7908	Intermediate Similarity	NPC67654
0.7905	Intermediate Similarity	NPC476944
0.7902	Intermediate Similarity	NPC265793
0.7902	Intermediate Similarity	NPC14650
0.7899	Intermediate Similarity	NPC23086
0.7898	Intermediate Similarity	NPC285567
0.7898	Intermediate Similarity	NPC472780
0.7898	Intermediate Similarity	NPC472783
0.7895	Intermediate Similarity	NPC473966
0.7895	Intermediate Similarity	NPC472421
0.7887	Intermediate Similarity	NPC218838
0.7885	Intermediate Similarity	NPC8389
0.7883	Intermediate Similarity	NPC65735
0.7883	Intermediate Similarity	NPC188377
0.7881	Intermediate Similarity	NPC125182
0.7881	Intermediate Similarity	NPC191634
0.7881	Intermediate Similarity	NPC472654
0.7881	Intermediate Similarity	NPC69647
0.7877	Intermediate Similarity	NPC473681
0.7877	Intermediate Similarity	NPC218204
0.7877	Intermediate Similarity	NPC148374
0.7877	Intermediate Similarity	NPC61157
0.7875	Intermediate Similarity	NPC476459
0.7872	Intermediate Similarity	NPC89133
0.7872	Intermediate Similarity	NPC61788

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 NPC473268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	856
0.2-0.3	1744
0.3-0.4	2606
0.4-0.5	2076
0.5-0.6	1154
0.6-0.7	379
0.7-0.8	59
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
0.7857	Intermediate Similarity	NPD5760	Phase 2
0.7857	Intermediate Similarity	NPD5761	Phase 2
0.7808	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7589	Intermediate Similarity	NPD5647	Approved
0.7568	Intermediate Similarity	NPD2344	Approved
0.747	Intermediate Similarity	NPD6559	Discontinued
0.7432	Intermediate Similarity	NPD2799	Discontinued
0.7372	Intermediate Similarity	NPD9092	Discovery
0.7368	Intermediate Similarity	NPD2309	Approved
0.7355	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6002	Phase 3
0.7333	Intermediate Similarity	NPD6004	Phase 3
0.7333	Intermediate Similarity	NPD6005	Phase 3
0.7325	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD3882	Suspended
0.7305	Intermediate Similarity	NPD9717	Approved
0.7297	Intermediate Similarity	NPD6653	Approved
0.7296	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1549	Phase 2
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2796	Approved
0.726	Intermediate Similarity	NPD2313	Discontinued
0.725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5402	Approved
0.7244	Intermediate Similarity	NPD5403	Approved
0.7241	Intermediate Similarity	NPD6832	Phase 2
0.7234	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1934	Approved
0.723	Intermediate Similarity	NPD447	Suspended
0.723	Intermediate Similarity	NPD6355	Discontinued
0.7229	Intermediate Similarity	NPD3818	Discontinued
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7033	Discontinued
0.719	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5494	Approved
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.7161	Intermediate Similarity	NPD6799	Approved
0.716	Intermediate Similarity	NPD3749	Approved
0.7125	Intermediate Similarity	NPD6801	Discontinued
0.7124	Intermediate Similarity	NPD2800	Approved
0.7124	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5401	Approved
0.7108	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6599	Discontinued
0.7105	Intermediate Similarity	NPD2346	Discontinued
0.7105	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1510	Phase 2
0.7081	Intermediate Similarity	NPD2801	Approved
0.7081	Intermediate Similarity	NPD7819	Suspended
0.708	Intermediate Similarity	NPD1241	Discontinued
0.7076	Intermediate Similarity	NPD8312	Approved
0.7076	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD6765	Approved
0.7059	Intermediate Similarity	NPD6764	Approved
0.7055	Intermediate Similarity	NPD9494	Approved
0.7047	Intermediate Similarity	NPD1240	Approved
0.7044	Intermediate Similarity	NPD3226	Approved
0.7039	Intermediate Similarity	NPD5712	Approved
0.7039	Intermediate Similarity	NPD2935	Discontinued
0.7034	Intermediate Similarity	NPD6362	Approved
0.7034	Intermediate Similarity	NPD2797	Approved
0.7034	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD1247	Approved
0.7027	Intermediate Similarity	NPD3764	Approved
0.7027	Intermediate Similarity	NPD3268	Approved
0.7019	Intermediate Similarity	NPD6844	Discontinued
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2534	Approved
0.7006	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4662	Approved
0.7006	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7768	Phase 2
0.6986	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1019	Discontinued
0.6982	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7157	Approved
0.6974	Remote Similarity	NPD4308	Phase 3
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3750	Approved
0.6966	Remote Similarity	NPD1876	Approved
0.6962	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD7411	Suspended
0.6954	Remote Similarity	NPD1607	Approved
0.6944	Remote Similarity	NPD1608	Approved
0.6943	Remote Similarity	NPD1511	Approved
0.6941	Remote Similarity	NPD7074	Phase 3
0.6937	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD411	Approved
0.6909	Remote Similarity	NPD919	Approved
0.6903	Remote Similarity	NPD1243	Approved
0.6899	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6784	Approved
0.6897	Remote Similarity	NPD6785	Approved
0.689	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7843	Approved
0.6882	Remote Similarity	NPD7054	Approved
0.6867	Remote Similarity	NPD6233	Phase 2
0.6861	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1512	Approved
0.6845	Remote Similarity	NPD3926	Phase 2
0.6842	Remote Similarity	NPD7472	Approved
0.6839	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2684	Approved
0.6832	Remote Similarity	NPD2649	Approved
0.6832	Remote Similarity	NPD2651	Approved
0.6831	Remote Similarity	NPD9545	Approved
0.6829	Remote Similarity	NPD2296	Approved
0.6829	Remote Similarity	NPD3817	Phase 2
0.6828	Remote Similarity	NPD3972	Approved
0.6824	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6100	Approved
0.6818	Remote Similarity	NPD6099	Approved
0.681	Remote Similarity	NPD6279	Approved
0.681	Remote Similarity	NPD6280	Approved
0.6809	Remote Similarity	NPD9493	Approved
0.6803	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6798	Discontinued
0.6786	Remote Similarity	NPD6808	Phase 2
0.6786	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD230	Phase 1
0.6774	Remote Similarity	NPD5763	Approved
0.6774	Remote Similarity	NPD5762	Approved
0.6768	Remote Similarity	NPD7972	Discontinued
0.6765	Remote Similarity	NPD290	Approved
0.6763	Remote Similarity	NPD7251	Discontinued
0.6763	Remote Similarity	NPD7685	Pre-registration
0.6753	Remote Similarity	NPD3748	Approved
0.6736	Remote Similarity	NPD17	Approved
0.6728	Remote Similarity	NPD7458	Discontinued
0.6727	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8127	Discontinued
0.6726	Remote Similarity	NPD6959	Discontinued
0.6725	Remote Similarity	NPD3751	Discontinued
0.6725	Remote Similarity	NPD2163	Approved
0.6724	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7808	Phase 3
0.6719	Remote Similarity	NPD8404	Phase 2
0.6711	Remote Similarity	NPD4307	Phase 2
0.6709	Remote Similarity	NPD3887	Approved
0.6709	Remote Similarity	NPD2354	Approved
0.6707	Remote Similarity	NPD7577	Discontinued
0.6706	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6797	Phase 2
0.6704	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3496	Discontinued
0.6689	Remote Similarity	NPD3266	Approved
0.6689	Remote Similarity	NPD3267	Approved
0.6688	Remote Similarity	NPD7097	Phase 1
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD7440	Discontinued
0.6646	Remote Similarity	NPD4110	Phase 3
0.6646	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4062	Phase 3
0.6644	Remote Similarity	NPD1091	Approved
0.6629	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5958	Discontinued
0.6623	Remote Similarity	NPD7095	Approved
0.6623	Remote Similarity	NPD6651	Approved
0.6622	Remote Similarity	NPD8651	Approved
0.662	Remote Similarity	NPD6671	Approved
0.6609	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2403	Approved
0.6606	Remote Similarity	NPD37	Approved
0.6601	Remote Similarity	NPD3142	Approved
0.6601	Remote Similarity	NPD3140	Approved
0.66	Remote Similarity	NPD2861	Phase 2
0.6594	Remote Similarity	NPD2182	Approved
0.659	Remote Similarity	NPD7286	Phase 2
0.6588	Remote Similarity	NPD3787	Discontinued
0.6587	Remote Similarity	NPD4967	Phase 2
0.6587	Remote Similarity	NPD4966	Approved
0.6587	Remote Similarity	NPD4965	Approved
0.6579	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1470	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