NPASS Compound

Structure

CID121275 OpenBabel06191715472D 33 37 0 0 1 0 0 0 0 0999 V2000 4.3301 -4.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -0.0000 -3.0000 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 -3.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 6.0622 -0.5000 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 2.5981 -3.5000 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 5.1962 1.0000 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 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 4.3301 -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 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 5 7 1 0 0 0 0 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 10 19 1 0 0 0 0 10 23 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 26 1 0 0 0 0 13 20 2 0 0 0 0 13 25 1 0 0 0 0 14 21 2 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 4 1 1 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 9 1 6 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 9 1 6 0 0 0 22 28 1 0 0 0 0 23 29 1 6 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 27 2 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.27
Volume:	474.101
LogP:	3.381
LogD:	3.626
LogS:	-1.946
# Rotatable Bonds:	5
TPSA:	74.19
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	4.033
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.445
MDCK Permeability:	1.3230792319518514e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.476

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.248
Plasma Protein Binding (PPB):	56.519779205322266%
Volume Distribution (VD):	2.047
Pgp-substrate:	23.479854583740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.372
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	12.578
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.831
Human Hepatotoxicity (H-HT):	0.378
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.17
Rat Oral Acute Toxicity:	0.674
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.944
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.706

Download Data

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

Natural Product: NPC121275

Natural Product ID:	NPC121275
*Common Name:**	7'-O-Demethylisocephaeline
IUPAC Name:	(1S)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Synonyms:	7'-O-Demethylisocephaeline
Standard InCHIKey:	HGQNZTBYUKKJLH-CQOCVSQPSA-N
Standard InCHI:	InChI=1S/C27H36N2O4/c1-4-16-15-29-8-6-18-12-26(32-2)27(33-3)14-21(18)23(29)10-19(16)9-22-20-13-25(31)24(30)11-17(20)5-7-28-22/h11-14,16,19,22-23,28,30-31H,4-10,15H2,1-3H3/t16-,19-,22-,23-/m0/s1
SMILES:	CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@@H]1NCCc2c1cc(O)c(c2)O)cc(c(c3)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519546
PubChem CID:	10884902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002659] Emetine alkaloids

*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
NPO18851	Psychotria klugii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880315]
NPO18851	Psychotria klugii	Species	Rubiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[12880315]
NPO18851	Psychotria klugii	Species	Rubiaceae	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	3
Others	3

Activity Type	# Activity
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	7.5	ug.mL-1	PMID[523742]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.5	ug.mL-1	PMID[523742]
NPT2	Others	Unspecified		Ratio IC50	>	7.0	n.a.	PMID[523742]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.067	ug.mL-1	PMID[523742]
NPT2	Others	Unspecified		Ratio IC50	>	3.0	n.a.	PMID[523742]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	19.0	ug.mL-1	PMID[523742]

☑ 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 NPC121275 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	275
0.1-0.2	1416
0.2-0.3	7057
0.3-0.4	10914
0.4-0.5	6821
0.5-0.6	11919
0.6-0.7	3407
0.7-0.8	576
0.8-0.85	204
0.85-0.9	73
0.9-0.95	31
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4138
1.0	High Similarity	NPC284183
0.9744	High Similarity	NPC109925
0.9539	High Similarity	NPC80129
0.9539	High Similarity	NPC187022
0.9276	High Similarity	NPC220858
0.9276	High Similarity	NPC88249
0.9276	High Similarity	NPC192768
0.9276	High Similarity	NPC97221
0.9276	High Similarity	NPC151895
0.9216	High Similarity	NPC277669
0.9216	High Similarity	NPC76213
0.9193	High Similarity	NPC108434
0.9193	High Similarity	NPC475215
0.9085	High Similarity	NPC207824
0.9085	High Similarity	NPC60538
0.9038	High Similarity	NPC276588
0.9038	High Similarity	NPC207757
0.9038	High Similarity	NPC204828
0.9038	High Similarity	NPC295691
0.9038	High Similarity	NPC39701
0.9038	High Similarity	NPC172765
0.9038	High Similarity	NPC110416
0.9038	High Similarity	NPC189266
0.9038	High Similarity	NPC278799
0.9038	High Similarity	NPC54379
0.9038	High Similarity	NPC127674
0.9038	High Similarity	NPC184026
0.9038	High Similarity	NPC2413
0.9038	High Similarity	NPC469817
0.9038	High Similarity	NPC5238
0.9038	High Similarity	NPC249797
0.9038	High Similarity	NPC193949
0.902	High Similarity	NPC428
0.902	High Similarity	NPC246587
0.902	High Similarity	NPC476571
0.902	High Similarity	NPC135538
0.902	High Similarity	NPC24233
0.902	High Similarity	NPC147390
0.8974	High Similarity	NPC477564
0.8974	High Similarity	NPC2295
0.8954	High Similarity	NPC321505
0.8954	High Similarity	NPC179825
0.8954	High Similarity	NPC191376
0.8951	High Similarity	NPC66573
0.8944	High Similarity	NPC42549
0.8944	High Similarity	NPC240841
0.8944	High Similarity	NPC256012
0.8944	High Similarity	NPC250846
0.8944	High Similarity	NPC317272
0.8944	High Similarity	NPC268503
0.8882	High Similarity	NPC294249
0.8868	High Similarity	NPC111485
0.8824	High Similarity	NPC185838
0.882	High Similarity	NPC475393
0.8816	High Similarity	NPC128019
0.8816	High Similarity	NPC476567
0.8816	High Similarity	NPC136860
0.8721	High Similarity	NPC60295
0.8721	High Similarity	NPC191132
0.8718	High Similarity	NPC477565
0.8718	High Similarity	NPC103379
0.8712	High Similarity	NPC81247
0.8712	High Similarity	NPC35627
0.8712	High Similarity	NPC476573
0.8671	High Similarity	NPC37272
0.8667	High Similarity	NPC477562
0.8667	High Similarity	NPC26240
0.8667	High Similarity	NPC69712
0.8663	High Similarity	NPC48490
0.8663	High Similarity	NPC175890
0.8663	High Similarity	NPC82457
0.8663	High Similarity	NPC274661
0.8663	High Similarity	NPC11296
0.8654	High Similarity	NPC7467
0.865	High Similarity	NPC276944
0.865	High Similarity	NPC24465
0.865	High Similarity	NPC232514
0.865	High Similarity	NPC238530
0.8598	High Similarity	NPC264850
0.8598	High Similarity	NPC13916
0.859	High Similarity	NPC16107
0.859	High Similarity	NPC210437
0.859	High Similarity	NPC476144
0.859	High Similarity	NPC106295
0.859	High Similarity	NPC51957
0.859	High Similarity	NPC476151
0.8563	High Similarity	NPC477020
0.8563	High Similarity	NPC192135
0.8563	High Similarity	NPC66341
0.8562	High Similarity	NPC188163
0.8562	High Similarity	NPC328750
0.8562	High Similarity	NPC474915
0.8562	High Similarity	NPC213206
0.8519	High Similarity	NPC216816
0.8509	High Similarity	NPC247639
0.8509	High Similarity	NPC25084
0.8497	Intermediate Similarity	NPC323123
0.8497	Intermediate Similarity	NPC314682
0.8487	Intermediate Similarity	NPC253429
0.8476	Intermediate Similarity	NPC324144
0.8466	Intermediate Similarity	NPC166014
0.8466	Intermediate Similarity	NPC27410
0.8431	Intermediate Similarity	NPC211468
0.8431	Intermediate Similarity	NPC170170
0.8431	Intermediate Similarity	NPC219233
0.843	Intermediate Similarity	NPC167116
0.843	Intermediate Similarity	NPC274716
0.843	Intermediate Similarity	NPC254441
0.8424	Intermediate Similarity	NPC253043
0.8424	Intermediate Similarity	NPC306843
0.8424	Intermediate Similarity	NPC136508
0.8424	Intermediate Similarity	NPC196447
0.8424	Intermediate Similarity	NPC96603
0.8424	Intermediate Similarity	NPC78222
0.8424	Intermediate Similarity	NPC212794
0.8424	Intermediate Similarity	NPC477563
0.8424	Intermediate Similarity	NPC13504
0.8421	Intermediate Similarity	NPC131204
0.8421	Intermediate Similarity	NPC301050
0.8421	Intermediate Similarity	NPC286119
0.8409	Intermediate Similarity	NPC256124
0.8395	Intermediate Similarity	NPC186063
0.8372	Intermediate Similarity	NPC15414
0.8372	Intermediate Similarity	NPC7715
0.8372	Intermediate Similarity	NPC279228
0.8372	Intermediate Similarity	NPC239824
0.8372	Intermediate Similarity	NPC104196
0.8372	Intermediate Similarity	NPC271013
0.8372	Intermediate Similarity	NPC49075
0.8372	Intermediate Similarity	NPC222661
0.8372	Intermediate Similarity	NPC90998
0.8372	Intermediate Similarity	NPC42663
0.8372	Intermediate Similarity	NPC182052
0.8372	Intermediate Similarity	NPC311973
0.8372	Intermediate Similarity	NPC290582
0.8372	Intermediate Similarity	NPC30779
0.8372	Intermediate Similarity	NPC328155
0.8372	Intermediate Similarity	NPC217748
0.8372	Intermediate Similarity	NPC229373
0.8372	Intermediate Similarity	NPC223690
0.8372	Intermediate Similarity	NPC258657
0.8372	Intermediate Similarity	NPC290005
0.8372	Intermediate Similarity	NPC181796
0.8372	Intermediate Similarity	NPC251735
0.8372	Intermediate Similarity	NPC54654
0.8372	Intermediate Similarity	NPC185639
0.8372	Intermediate Similarity	NPC285931
0.8372	Intermediate Similarity	NPC8836
0.8363	Intermediate Similarity	NPC474507
0.8354	Intermediate Similarity	NPC205167
0.8323	Intermediate Similarity	NPC233029
0.8323	Intermediate Similarity	NPC158376
0.8323	Intermediate Similarity	NPC12053
0.8323	Intermediate Similarity	NPC117188
0.8323	Intermediate Similarity	NPC306555
0.8323	Intermediate Similarity	NPC145832
0.8323	Intermediate Similarity	NPC82285
0.8323	Intermediate Similarity	NPC133011
0.8323	Intermediate Similarity	NPC474931
0.8323	Intermediate Similarity	NPC210148
0.8323	Intermediate Similarity	NPC205421
0.8323	Intermediate Similarity	NPC81218
0.8314	Intermediate Similarity	NPC312918
0.8314	Intermediate Similarity	NPC477561
0.8314	Intermediate Similarity	NPC239584
0.8314	Intermediate Similarity	NPC476574
0.8314	Intermediate Similarity	NPC155442
0.8282	Intermediate Similarity	NPC203784
0.8282	Intermediate Similarity	NPC146288
0.8282	Intermediate Similarity	NPC147091
0.8282	Intermediate Similarity	NPC170503
0.8282	Intermediate Similarity	NPC126519
0.8256	Intermediate Similarity	NPC475479
0.8256	Intermediate Similarity	NPC243454
0.825	Intermediate Similarity	NPC92541
0.8246	Intermediate Similarity	NPC148709
0.8246	Intermediate Similarity	NPC173416
0.8246	Intermediate Similarity	NPC476577
0.8242	Intermediate Similarity	NPC249274
0.8229	Intermediate Similarity	NPC116465
0.8229	Intermediate Similarity	NPC212237
0.8224	Intermediate Similarity	NPC160692
0.8221	Intermediate Similarity	NPC41178
0.8221	Intermediate Similarity	NPC138487
0.8221	Intermediate Similarity	NPC216459
0.8218	Intermediate Similarity	NPC135772
0.8214	Intermediate Similarity	NPC210140
0.8193	Intermediate Similarity	NPC60186
0.8187	Intermediate Similarity	NPC475959
0.8182	Intermediate Similarity	NPC22115
0.8182	Intermediate Similarity	NPC275680
0.8176	Intermediate Similarity	NPC239775
0.8166	Intermediate Similarity	NPC83198
0.8166	Intermediate Similarity	NPC204908
0.8158	Intermediate Similarity	NPC33338
0.8158	Intermediate Similarity	NPC302171
0.8158	Intermediate Similarity	NPC300020
0.815	Intermediate Similarity	NPC32154
0.8148	Intermediate Similarity	NPC476568

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 NPC121275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	633
0.2-0.3	1017
0.3-0.4	1735
0.4-0.5	2791
0.5-0.6	1870
0.6-0.7	711
0.7-0.8	199
0.8-0.85	23
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD7298	Approved
0.859	High Similarity	NPD4584	Approved
0.8562	High Similarity	NPD4664	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4772	Phase 2
0.8385	Intermediate Similarity	NPD4773	Phase 2
0.8372	Intermediate Similarity	NPD8053	Approved
0.8372	Intermediate Similarity	NPD8054	Approved
0.8313	Intermediate Similarity	NPD6107	Approved
0.8263	Intermediate Similarity	NPD4010	Discontinued
0.825	Intermediate Similarity	NPD6031	Approved
0.825	Intermediate Similarity	NPD6030	Approved
0.8228	Intermediate Similarity	NPD3845	Phase 1
0.8228	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3639	Approved
0.8137	Intermediate Similarity	NPD3640	Phase 3
0.8137	Intermediate Similarity	NPD3641	Approved
0.8077	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD4166	Phase 2
0.8036	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6297	Approved
0.7965	Intermediate Similarity	NPD8099	Discontinued
0.7965	Intermediate Similarity	NPD8252	Approved
0.7965	Intermediate Similarity	NPD8251	Approved
0.7955	Intermediate Similarity	NPD6851	Approved
0.7955	Intermediate Similarity	NPD6853	Approved
0.7952	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3124	Discontinued
0.7943	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4017	Approved
0.7919	Intermediate Similarity	NPD8156	Discontinued
0.7917	Intermediate Similarity	NPD7833	Phase 2
0.7917	Intermediate Similarity	NPD7831	Phase 2
0.7917	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD2898	Approved
0.784	Intermediate Similarity	NPD7598	Phase 2
0.7826	Intermediate Similarity	NPD5241	Discontinued
0.7812	Intermediate Similarity	NPD3060	Approved
0.7753	Intermediate Similarity	NPD6618	Phase 2
0.775	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2489	Approved
0.7746	Intermediate Similarity	NPD27	Approved
0.7742	Intermediate Similarity	NPD5718	Phase 2
0.7738	Intermediate Similarity	NPD2977	Approved
0.7738	Intermediate Similarity	NPD2978	Approved
0.773	Intermediate Similarity	NPD2420	Approved
0.773	Intermediate Similarity	NPD2421	Approved
0.7673	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3053	Approved
0.7647	Intermediate Similarity	NPD3055	Approved
0.7628	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5312	Approved
0.7614	Intermediate Similarity	NPD5313	Approved
0.761	Intermediate Similarity	NPD6896	Approved
0.761	Intermediate Similarity	NPD6895	Approved
0.76	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7313	Approved
0.7598	Intermediate Similarity	NPD7311	Approved
0.7598	Intermediate Similarity	NPD7312	Approved
0.7598	Intermediate Similarity	NPD7310	Approved
0.7593	Intermediate Similarity	NPD4162	Approved
0.7586	Intermediate Similarity	NPD2970	Approved
0.7586	Intermediate Similarity	NPD2969	Approved
0.7582	Intermediate Similarity	NPD5310	Approved
0.7582	Intermediate Similarity	NPD5311	Approved
0.7572	Intermediate Similarity	NPD7802	Discontinued
0.7571	Intermediate Similarity	NPD7479	Phase 2
0.7564	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7309	Approved
0.7544	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6071	Discontinued
0.7529	Intermediate Similarity	NPD3051	Approved
0.747	Intermediate Similarity	NPD1424	Approved
0.7468	Intermediate Similarity	NPD2674	Phase 3
0.7442	Intermediate Similarity	NPD6788	Approved
0.7432	Intermediate Similarity	NPD7906	Approved
0.7425	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3145	Approved
0.7405	Intermediate Similarity	NPD3144	Approved
0.7403	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4083	Discontinued
0.7378	Intermediate Similarity	NPD5177	Phase 3
0.7348	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD817	Approved
0.7329	Intermediate Similarity	NPD5314	Approved
0.7329	Intermediate Similarity	NPD823	Approved
0.7322	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7153	Discontinued
0.731	Intermediate Similarity	NPD7110	Phase 1
0.731	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4577	Approved
0.7308	Intermediate Similarity	NPD4578	Approved
0.7287	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4663	Approved
0.7283	Intermediate Similarity	NPD2563	Approved
0.7283	Intermediate Similarity	NPD2560	Approved
0.7278	Intermediate Similarity	NPD2122	Discontinued
0.7267	Intermediate Similarity	NPD5720	Discontinued
0.7256	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7124	Phase 2
0.7225	Intermediate Similarity	NPD6612	Phase 2
0.7222	Intermediate Similarity	NPD6042	Phase 2
0.7222	Intermediate Similarity	NPD42	Phase 2
0.7219	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7526	Approved
0.7219	Intermediate Similarity	NPD52	Approved
0.7219	Intermediate Similarity	NPD6090	Discontinued
0.7213	Intermediate Similarity	NPD7281	Phase 3
0.7213	Intermediate Similarity	NPD7280	Phase 3
0.7212	Intermediate Similarity	NPD4257	Approved
0.7212	Intermediate Similarity	NPD4256	Phase 2
0.7205	Intermediate Similarity	NPD3109	Approved
0.7205	Intermediate Similarity	NPD3062	Approved
0.7205	Intermediate Similarity	NPD3061	Approved
0.7205	Intermediate Similarity	NPD3059	Approved
0.7205	Intermediate Similarity	NPD3110	Approved
0.7191	Intermediate Similarity	NPD6687	Approved
0.7191	Intermediate Similarity	NPD6688	Approved
0.7186	Intermediate Similarity	NPD5160	Discontinued
0.7186	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5977	Approved
0.7184	Intermediate Similarity	NPD5978	Approved
0.7176	Intermediate Similarity	NPD4727	Phase 1
0.7173	Intermediate Similarity	NPD8095	Phase 1
0.7169	Intermediate Similarity	NPD2459	Approved
0.7169	Intermediate Similarity	NPD2458	Approved
0.7169	Intermediate Similarity	NPD2460	Phase 3
0.7167	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD2490	Approved
0.7166	Intermediate Similarity	NPD2488	Approved
0.716	Intermediate Similarity	NPD2874	Phase 2
0.716	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3645	Discontinued
0.7158	Intermediate Similarity	NPD7034	Discontinued
0.7151	Intermediate Similarity	NPD4481	Phase 3
0.7151	Intermediate Similarity	NPD7291	Discontinued
0.7151	Intermediate Similarity	NPD6876	Approved
0.7151	Intermediate Similarity	NPD6875	Approved
0.7143	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1132	Approved
0.7143	Intermediate Similarity	NPD1130	Approved
0.7143	Intermediate Similarity	NPD1136	Approved
0.7134	Intermediate Similarity	NPD1753	Discontinued
0.7119	Intermediate Similarity	NPD4666	Phase 3
0.7117	Intermediate Similarity	NPD2653	Approved
0.7093	Intermediate Similarity	NPD4005	Discontinued
0.7085	Intermediate Similarity	NPD7827	Phase 1
0.7083	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD597	Approved
0.7081	Intermediate Similarity	NPD601	Approved
0.7081	Intermediate Similarity	NPD598	Approved
0.7076	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5709	Phase 3
0.7059	Intermediate Similarity	NPD4123	Phase 3
0.7059	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2120	Phase 2
0.7037	Intermediate Similarity	NPD3531	Approved
0.7037	Intermediate Similarity	NPD3532	Approved
0.7037	Intermediate Similarity	NPD3530	Approved
0.7033	Intermediate Similarity	NPD4873	Discontinued
0.7032	Intermediate Similarity	NPD2668	Approved
0.7032	Intermediate Similarity	NPD2667	Approved
0.703	Intermediate Similarity	NPD2155	Approved
0.703	Intermediate Similarity	NPD2156	Approved
0.703	Intermediate Similarity	NPD2154	Approved
0.7029	Intermediate Similarity	NPD5772	Approved
0.7029	Intermediate Similarity	NPD4585	Approved
0.7029	Intermediate Similarity	NPD5773	Approved
0.7027	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5155	Approved
0.7019	Intermediate Similarity	NPD5156	Approved
0.7018	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2989	Phase 2
0.7012	Intermediate Similarity	NPD3054	Approved
0.7012	Intermediate Similarity	NPD3052	Approved
0.7012	Intermediate Similarity	NPD2986	Phase 2
0.7006	Intermediate Similarity	NPD5604	Discontinued
0.7006	Intermediate Similarity	NPD4055	Discovery
0.7006	Intermediate Similarity	NPD2232	Approved
0.7006	Intermediate Similarity	NPD2230	Approved
0.7006	Intermediate Similarity	NPD2233	Approved
0.7	Intermediate Similarity	NPD3635	Approved
0.7	Intermediate Similarity	NPD3636	Approved
0.7	Intermediate Similarity	NPD3637	Approved
0.6995	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD824	Approved
0.699	Remote Similarity	NPD4040	Phase 1
0.6989	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3156	Discontinued

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