NPASS Compound

Structure

NPC474615 OpenBabel07101719152D 27 30 0 0 1 0 0 0 0 0999 V2000 1.5505 -5.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1640 -5.1886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 1.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3074 0.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2153 -4.5502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8965 -3.6848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4832 -1.5907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0029 -0.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7644 -4.8170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3120 0.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9067 -3.8272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4832 -2.5502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5436 -1.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6523 -3.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6523 -1.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9067 -0.3138 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8965 -0.4561 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0029 -3.4117 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5436 -2.5705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3493 -3.0502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7251 -0.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2153 -2.5502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6701 -0.3013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3493 -4.0502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9340 -2.0705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0018 -3.4593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 24 1 0 0 0 0 6 11 1 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 15 2 0 0 0 0 8 13 2 0 0 0 0 11 9 1 6 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 10 1 1 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 13 1 1 0 0 0 19 27 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	374.469
LogP:	4.712
LogD:	4.089
LogS:	-5.567
# Rotatable Bonds:	4
TPSA:	85.34
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	6.275
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.71
MDCK Permeability:	2.0282379409763962e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.788

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	95.71317291259766%
Volume Distribution (VD):	1.04
Pgp-substrate:	4.107425689697266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.814
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.577

ADMET: Excretion

Clearance (CL):	10.882
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.952
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.809
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.05
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC474615

Natural Product ID:	NPC474615
*Common Name:**	Pseudopterolide
IUPAC Name:	n.a.
Synonyms:	Pseudopterolide
Standard InCHIKey:	SNGMXRAYMWQRSS-ZMKKGPNFSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-9(2)11-6-14-12(20(22)24-5)7-15(25-14)17(10(3)4)16-8-13(21(23)26-16)19-18(11)27-19/h7-9,11,16-19H,3,6H2,1-2,4-5H3/t11-,16-,17+,18-,19+/m1/s1
SMILES:	COC(=O)c1cc2oc1C[C@H](C(C)C)[C@H]1O[C@H]1C1=C[C@H]([C@H]2C(=C)C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476887
PubChem CID:	44584546
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000076] Furans [CHEMONTID:0004758] Furoic acid and derivatives [CHEMONTID:0004805] Furoic acid esters

*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
NPO33065	Pseudopterogorgia	Genus	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2895165]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		ED50	=	8.0	ug ml-1	PMID[515867]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	83.0	%	PMID[515867]

☑ 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 NPC474615 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	368
0.1-0.2	1535
0.2-0.3	4088
0.3-0.4	9078
0.4-0.5	10315
0.5-0.6	6563
0.6-0.7	8224
0.7-0.8	2472
0.8-0.85	26
0.85-0.9	17
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC37488
0.9389	High Similarity	NPC136340
0.9281	High Similarity	NPC195920
0.9275	High Similarity	NPC254198
0.9149	High Similarity	NPC474317
0.9118	High Similarity	NPC286130
0.9111	High Similarity	NPC159786
0.9078	High Similarity	NPC104924
0.9078	High Similarity	NPC475864
0.9058	High Similarity	NPC282973
0.9021	High Similarity	NPC475904
0.9021	High Similarity	NPC474270
0.9	High Similarity	NPC110305
0.8951	High Similarity	NPC474255
0.8951	High Similarity	NPC474220
0.8951	High Similarity	NPC471618
0.8741	High Similarity	NPC45947
0.8707	High Similarity	NPC474219
0.8707	High Similarity	NPC474378
0.8592	High Similarity	NPC248795
0.8582	High Similarity	NPC107571
0.8489	Intermediate Similarity	NPC106247
0.8489	Intermediate Similarity	NPC200718
0.8472	Intermediate Similarity	NPC22248
0.8444	Intermediate Similarity	NPC216810
0.8435	Intermediate Similarity	NPC19747
0.8425	Intermediate Similarity	NPC62799
0.8369	Intermediate Similarity	NPC303217
0.8288	Intermediate Similarity	NPC84479
0.8219	Intermediate Similarity	NPC223415
0.8212	Intermediate Similarity	NPC470380
0.8182	Intermediate Similarity	NPC473268
0.817	Intermediate Similarity	NPC474542
0.8163	Intermediate Similarity	NPC261733
0.8163	Intermediate Similarity	NPC307346
0.8163	Intermediate Similarity	NPC267004
0.8163	Intermediate Similarity	NPC218712
0.8158	Intermediate Similarity	NPC114880
0.8151	Intermediate Similarity	NPC470856
0.8148	Intermediate Similarity	NPC323118
0.8133	Intermediate Similarity	NPC211625
0.8121	Intermediate Similarity	NPC221809
0.8121	Intermediate Similarity	NPC224418
0.8095	Intermediate Similarity	NPC470741
0.8095	Intermediate Similarity	NPC205071
0.8074	Intermediate Similarity	NPC1848
0.8071	Intermediate Similarity	NPC21460
0.806	Intermediate Similarity	NPC244862
0.806	Intermediate Similarity	NPC67345
0.8028	Intermediate Similarity	NPC470740
0.8027	Intermediate Similarity	NPC473152
0.8026	Intermediate Similarity	NPC191104
0.8013	Intermediate Similarity	NPC329180
0.8	Intermediate Similarity	NPC220094
0.8	Intermediate Similarity	NPC81405
0.8	Intermediate Similarity	NPC476943
0.7987	Intermediate Similarity	NPC184702
0.7986	Intermediate Similarity	NPC137570
0.7986	Intermediate Similarity	NPC146872
0.7975	Intermediate Similarity	NPC472664
0.7974	Intermediate Similarity	NPC75906
0.7973	Intermediate Similarity	NPC297985
0.7961	Intermediate Similarity	NPC88445
0.7958	Intermediate Similarity	NPC196979
0.7958	Intermediate Similarity	NPC470976
0.7958	Intermediate Similarity	NPC470977
0.7949	Intermediate Similarity	NPC140952
0.7949	Intermediate Similarity	NPC474611
0.7935	Intermediate Similarity	NPC278010
0.7935	Intermediate Similarity	NPC250769
0.7935	Intermediate Similarity	NPC104736
0.7935	Intermediate Similarity	NPC295608
0.7933	Intermediate Similarity	NPC233763
0.7931	Intermediate Similarity	NPC310830
0.7926	Intermediate Similarity	NPC473969
0.7919	Intermediate Similarity	NPC86935
0.7917	Intermediate Similarity	NPC92941
0.7917	Intermediate Similarity	NPC247743
0.7908	Intermediate Similarity	NPC18135
0.7898	Intermediate Similarity	NPC333139
0.7887	Intermediate Similarity	NPC282230
0.7887	Intermediate Similarity	NPC183348
0.7885	Intermediate Similarity	NPC304692
0.7885	Intermediate Similarity	NPC470625
0.7881	Intermediate Similarity	NPC10088
0.7881	Intermediate Similarity	NPC250228
0.7881	Intermediate Similarity	NPC107625
0.7877	Intermediate Similarity	NPC236532
0.7875	Intermediate Similarity	NPC473753
0.7875	Intermediate Similarity	NPC473766
0.7871	Intermediate Similarity	NPC131725
0.7871	Intermediate Similarity	NPC75310
0.7867	Intermediate Similarity	NPC10302
0.7867	Intermediate Similarity	NPC105381
0.7867	Intermediate Similarity	NPC470932
0.7862	Intermediate Similarity	NPC276735
0.7862	Intermediate Similarity	NPC56358
0.7862	Intermediate Similarity	NPC261184
0.7857	Intermediate Similarity	NPC95567
0.7857	Intermediate Similarity	NPC184391
0.7857	Intermediate Similarity	NPC319140
0.7852	Intermediate Similarity	NPC267632
0.7848	Intermediate Similarity	NPC115432
0.7848	Intermediate Similarity	NPC260296
0.7838	Intermediate Similarity	NPC472515
0.7838	Intermediate Similarity	NPC20500
0.7836	Intermediate Similarity	NPC45536
0.7834	Intermediate Similarity	NPC269495
0.7834	Intermediate Similarity	NPC473368
0.7832	Intermediate Similarity	NPC15083
0.7829	Intermediate Similarity	NPC61284
0.7829	Intermediate Similarity	NPC304443
0.7829	Intermediate Similarity	NPC113428
0.7829	Intermediate Similarity	NPC74539
0.7826	Intermediate Similarity	NPC472895
0.7821	Intermediate Similarity	NPC41880
0.7817	Intermediate Similarity	NPC66246
0.7817	Intermediate Similarity	NPC170546
0.7815	Intermediate Similarity	NPC294365
0.7815	Intermediate Similarity	NPC276676
0.7815	Intermediate Similarity	NPC171656
0.7808	Intermediate Similarity	NPC42400
0.7808	Intermediate Similarity	NPC470742
0.7808	Intermediate Similarity	NPC186626
0.7806	Intermediate Similarity	NPC67654
0.7806	Intermediate Similarity	NPC57998
0.7806	Intermediate Similarity	NPC308555
0.78	Intermediate Similarity	NPC471639
0.78	Intermediate Similarity	NPC471643
0.78	Intermediate Similarity	NPC313036
0.78	Intermediate Similarity	NPC142113
0.7792	Intermediate Similarity	NPC472406
0.7791	Intermediate Similarity	NPC120220
0.7785	Intermediate Similarity	NPC476349
0.7785	Intermediate Similarity	NPC476350
0.7785	Intermediate Similarity	NPC287559
0.7785	Intermediate Similarity	NPC40583
0.7785	Intermediate Similarity	NPC244750
0.7778	Intermediate Similarity	NPC474407
0.7778	Intermediate Similarity	NPC302392
0.7778	Intermediate Similarity	NPC474426
0.7778	Intermediate Similarity	NPC131801
0.7778	Intermediate Similarity	NPC293253
0.7778	Intermediate Similarity	NPC195325
0.7778	Intermediate Similarity	NPC227660
0.7778	Intermediate Similarity	NPC474425
0.7778	Intermediate Similarity	NPC320789
0.7771	Intermediate Similarity	NPC247677
0.7771	Intermediate Similarity	NPC160015
0.777	Intermediate Similarity	NPC188377
0.777	Intermediate Similarity	NPC36414
0.777	Intermediate Similarity	NPC65735
0.777	Intermediate Similarity	NPC470399
0.777	Intermediate Similarity	NPC118853
0.777	Intermediate Similarity	NPC148374
0.7764	Intermediate Similarity	NPC270312
0.7763	Intermediate Similarity	NPC470941
0.7763	Intermediate Similarity	NPC71821
0.7763	Intermediate Similarity	NPC308799
0.7756	Intermediate Similarity	NPC469850
0.7755	Intermediate Similarity	NPC268081
0.7755	Intermediate Similarity	NPC472376
0.7754	Intermediate Similarity	NPC270807
0.7754	Intermediate Similarity	NPC174915
0.7744	Intermediate Similarity	NPC472584
0.7742	Intermediate Similarity	NPC475777
0.7742	Intermediate Similarity	NPC156244
0.7742	Intermediate Similarity	NPC473732
0.7736	Intermediate Similarity	NPC188649
0.7736	Intermediate Similarity	NPC43971
0.7736	Intermediate Similarity	NPC300680
0.7736	Intermediate Similarity	NPC19554
0.7736	Intermediate Similarity	NPC74749
0.7736	Intermediate Similarity	NPC49009
0.7733	Intermediate Similarity	NPC471640
0.7733	Intermediate Similarity	NPC80635
0.7733	Intermediate Similarity	NPC471644
0.7733	Intermediate Similarity	NPC254010
0.7727	Intermediate Similarity	NPC469335
0.7727	Intermediate Similarity	NPC159927
0.7727	Intermediate Similarity	NPC156189
0.7727	Intermediate Similarity	NPC477404
0.7727	Intermediate Similarity	NPC196864
0.7727	Intermediate Similarity	NPC212257
0.7722	Intermediate Similarity	NPC260902
0.7722	Intermediate Similarity	NPC296957
0.7722	Intermediate Similarity	NPC474932
0.7718	Intermediate Similarity	NPC136095
0.7718	Intermediate Similarity	NPC262635
0.7712	Intermediate Similarity	NPC52106
0.7712	Intermediate Similarity	NPC473428
0.7708	Intermediate Similarity	NPC471545
0.7708	Intermediate Similarity	NPC45358
0.7708	Intermediate Similarity	NPC471544
0.7708	Intermediate Similarity	NPC473344
0.7707	Intermediate Similarity	NPC263265
0.7707	Intermediate Similarity	NPC209364
0.7707	Intermediate Similarity	NPC107646
0.7707	Intermediate Similarity	NPC60973
0.7707	Intermediate Similarity	NPC254163

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 NPC474615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	1026
0.2-0.3	2006
0.3-0.4	2727
0.4-0.5	1923
0.5-0.6	856
0.6-0.7	245
0.7-0.8	51
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7898	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD920	Approved
0.7718	Intermediate Similarity	NPD1243	Approved
0.7697	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2796	Approved
0.7566	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7467	Intermediate Similarity	NPD1471	Phase 3
0.7467	Intermediate Similarity	NPD2344	Approved
0.7467	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6808	Phase 2
0.7407	Intermediate Similarity	NPD5494	Approved
0.7403	Intermediate Similarity	NPD6799	Approved
0.7361	Intermediate Similarity	NPD1019	Discontinued
0.7355	Intermediate Similarity	NPD2533	Approved
0.7355	Intermediate Similarity	NPD2534	Approved
0.7355	Intermediate Similarity	NPD2532	Approved
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7819	Suspended
0.7284	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD3926	Phase 2
0.7255	Intermediate Similarity	NPD2800	Approved
0.7248	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD919	Approved
0.7234	Intermediate Similarity	NPD17	Approved
0.7208	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5760	Phase 2
0.7205	Intermediate Similarity	NPD5761	Phase 2
0.7203	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7411	Suspended
0.7178	Intermediate Similarity	NPD7075	Discontinued
0.717	Intermediate Similarity	NPD3226	Approved
0.7168	Intermediate Similarity	NPD8434	Phase 2
0.7162	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD6279	Approved
0.7134	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6002	Phase 3
0.7124	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6005	Phase 3
0.7124	Intermediate Similarity	NPD6004	Phase 3
0.7124	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD1551	Phase 2
0.7055	Intermediate Similarity	NPD3267	Approved
0.7055	Intermediate Similarity	NPD5402	Approved
0.7055	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD3266	Approved
0.7055	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1247	Approved
0.7044	Intermediate Similarity	NPD5403	Approved
0.7025	Intermediate Similarity	NPD5401	Approved
0.702	Intermediate Similarity	NPD447	Suspended
0.7013	Intermediate Similarity	NPD2346	Discontinued
0.7012	Intermediate Similarity	NPD3882	Suspended
0.7007	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2798	Approved
0.6994	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD7033	Discontinued
0.6986	Remote Similarity	NPD1876	Approved
0.697	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3972	Approved
0.6954	Remote Similarity	NPD1240	Approved
0.6948	Remote Similarity	NPD2935	Discontinued
0.6941	Remote Similarity	NPD3818	Discontinued
0.6939	Remote Similarity	NPD1203	Approved
0.6937	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3268	Approved
0.6933	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2654	Approved
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4380	Phase 2
0.6909	Remote Similarity	NPD7768	Phase 2
0.6909	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1933	Approved
0.6892	Remote Similarity	NPD5647	Approved
0.6879	Remote Similarity	NPD3750	Approved
0.6879	Remote Similarity	NPD6559	Discontinued
0.6863	Remote Similarity	NPD1607	Approved
0.6861	Remote Similarity	NPD2182	Approved
0.6857	Remote Similarity	NPD1241	Discontinued
0.6853	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD4307	Phase 2
0.6835	Remote Similarity	NPD3887	Approved
0.6824	Remote Similarity	NPD2403	Approved
0.6824	Remote Similarity	NPD2797	Approved
0.6821	Remote Similarity	NPD5953	Discontinued
0.6821	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD411	Approved
0.6813	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5585	Approved
0.6797	Remote Similarity	NPD230	Phase 1
0.6788	Remote Similarity	NPD2801	Approved
0.6784	Remote Similarity	NPD7473	Discontinued
0.6782	Remote Similarity	NPD6765	Approved
0.6782	Remote Similarity	NPD6764	Approved
0.6779	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2296	Approved
0.6747	Remote Similarity	NPD5353	Approved
0.6746	Remote Similarity	NPD6959	Discontinued
0.6713	Remote Similarity	NPD9493	Approved
0.6711	Remote Similarity	NPD3764	Approved
0.6706	Remote Similarity	NPD5710	Approved
0.6706	Remote Similarity	NPD6232	Discontinued
0.6706	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5711	Approved
0.6705	Remote Similarity	NPD7286	Phase 2
0.6688	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD5890	Approved
0.6667	Remote Similarity	NPD5889	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD1511	Approved
0.6646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6651	Approved
0.6629	Remote Similarity	NPD6785	Approved
0.6629	Remote Similarity	NPD6784	Approved
0.6628	Remote Similarity	NPD6166	Phase 2
0.6628	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3142	Approved
0.6623	Remote Similarity	NPD3140	Approved
0.661	Remote Similarity	NPD8312	Approved
0.661	Remote Similarity	NPD8313	Approved
0.6609	Remote Similarity	NPD5844	Phase 1
0.6609	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6362	Approved
0.6595	Remote Similarity	NPD8285	Discontinued
0.6594	Remote Similarity	NPD3134	Approved
0.6582	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2353	Approved
0.6581	Remote Similarity	NPD4622	Approved
0.6581	Remote Similarity	NPD4618	Approved
0.6577	Remote Similarity	NPD4359	Approved
0.6571	Remote Similarity	NPD7074	Phase 3
0.6571	Remote Similarity	NPD2067	Discontinued
0.657	Remote Similarity	NPD5242	Approved
0.6569	Remote Similarity	NPD164	Approved
0.6566	Remote Similarity	NPD6385	Approved
0.6566	Remote Similarity	NPD6386	Approved
0.6564	Remote Similarity	NPD2186	Approved
0.6564	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1512	Approved
0.6554	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3751	Discontinued
0.6538	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6653	Approved
0.6536	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1778	Approved
0.6519	Remote Similarity	NPD6100	Approved
0.6519	Remote Similarity	NPD6099	Approved
0.6516	Remote Similarity	NPD2979	Phase 3
0.6516	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7054	Approved
0.6512	Remote Similarity	NPD7229	Phase 3
0.6509	Remote Similarity	NPD4965	Approved
0.6509	Remote Similarity	NPD4966	Approved
0.6509	Remote Similarity	NPD4967	Phase 2
0.6506	Remote Similarity	NPD6585	Discontinued
0.6497	Remote Similarity	NPD7685	Pre-registration
0.6497	Remote Similarity	NPD5688	Approved
0.6497	Remote Similarity	NPD5689	Approved
0.6494	Remote Similarity	NPD1296	Phase 2
0.6486	Remote Similarity	NPD3496	Discontinued
0.6481	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7472	Approved
0.6467	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7199	Phase 2
0.6452	Remote Similarity	NPD6233	Phase 2
0.6452	Remote Similarity	NPD8032	Phase 2
0.6452	Remote Similarity	NPD4870	Approved
0.6446	Remote Similarity	NPD7458	Discontinued
0.6444	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6797	Phase 2
0.6437	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6234	Discontinued
0.6429	Remote Similarity	NPD1358	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