NPASS Compound

Structure

NPC196251 OpenBabel07101718252D 27 30 0 0 1 0 0 0 0 0999 V2000 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.8171 -4.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -4.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 24 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 4 1 6 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 6 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 6 0 0 0 21 23 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.21
Volume:	387.388
LogP:	4.162
LogD:	3.922
LogS:	-3.667
# Rotatable Bonds:	5
TPSA:	54.56
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	3.859
Fsp3:	0.5
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:	-4.919
MDCK Permeability:	2.6585361410980113e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	91.84622955322266%
Volume Distribution (VD):	1.501
Pgp-substrate:	4.777948379516602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.784
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.288
CYP2C9-substrate:	0.14
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	8.78
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.621
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.822
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.804
Carcinogencity:	0.913
Eye Corrosion:	0.005
Eye Irritation:	0.042
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC196251

Natural Product ID:	NPC196251
*Common Name:**	Corynantheidine
IUPAC Name:	methyl (Z)-2-[(2S,3S,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
Synonyms:	Corynantheidine
Standard InCHIKey:	NMLUOJBSAYAYEM-OCUKFOPLSA-N
Standard InCHI:	InChI=1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13-/t14-,17+,20+/m1/s1
SMILES:	CO/C=C(/[C@H]1C[C@@H]2N(C[C@H]1CC)CCc1c2[nH]c2c1cccc2)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668783
PubChem CID:	6540753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type 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
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	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	4

Activity Type	# Activity
Cell Line	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	13960.0	nM	PMID[494943]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	23280.0	nM	PMID[494943]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	>	30.0	ug.mL-1	PMID[494943]

☑ 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 NPC196251 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	1707
0.2-0.3	9230
0.3-0.4	20466
0.4-0.5	5698
0.5-0.6	2497
0.6-0.7	1982
0.7-0.8	706
0.8-0.85	72
0.85-0.9	25
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC102338
1.0	High Similarity	NPC63199
1.0	High Similarity	NPC111602
0.9435	High Similarity	NPC294909
0.9435	High Similarity	NPC128265
0.9435	High Similarity	NPC199851
0.9435	High Similarity	NPC312870
0.9435	High Similarity	NPC254240
0.9261	High Similarity	NPC220151
0.9261	High Similarity	NPC19692
0.9253	High Similarity	NPC472112
0.9195	High Similarity	NPC175474
0.9101	High Similarity	NPC245916
0.904	High Similarity	NPC472113
0.8793	High Similarity	NPC469896
0.8791	High Similarity	NPC52557
0.875	High Similarity	NPC258480
0.8743	High Similarity	NPC152768
0.8743	High Similarity	NPC148183
0.8737	High Similarity	NPC221100
0.8737	High Similarity	NPC234078
0.8696	High Similarity	NPC81654
0.8696	High Similarity	NPC79129
0.8696	High Similarity	NPC49196
0.8696	High Similarity	NPC313985
0.8696	High Similarity	NPC249150
0.8696	High Similarity	NPC195461
0.8644	High Similarity	NPC472119
0.8588	High Similarity	NPC271797
0.8588	High Similarity	NPC21174
0.8588	High Similarity	NPC143533
0.8587	High Similarity	NPC50503
0.8547	High Similarity	NPC66210
0.8523	High Similarity	NPC219336
0.8516	High Similarity	NPC55493
0.8513	High Similarity	NPC52254
0.8466	Intermediate Similarity	NPC15573
0.8466	Intermediate Similarity	NPC234987
0.8466	Intermediate Similarity	NPC183662
0.8466	Intermediate Similarity	NPC217372
0.8462	Intermediate Similarity	NPC82070
0.8407	Intermediate Similarity	NPC329858
0.8407	Intermediate Similarity	NPC314333
0.8398	Intermediate Similarity	NPC472323
0.8392	Intermediate Similarity	NPC21638
0.8371	Intermediate Similarity	NPC15840
0.837	Intermediate Similarity	NPC472210
0.837	Intermediate Similarity	NPC269886
0.837	Intermediate Similarity	NPC247735
0.837	Intermediate Similarity	NPC81802
0.837	Intermediate Similarity	NPC472295
0.8368	Intermediate Similarity	NPC238457
0.8333	Intermediate Similarity	NPC317430
0.8295	Intermediate Similarity	NPC472123
0.8295	Intermediate Similarity	NPC161861
0.8287	Intermediate Similarity	NPC79062
0.8287	Intermediate Similarity	NPC472107
0.8283	Intermediate Similarity	NPC472099
0.8265	Intermediate Similarity	NPC476114
0.825	Intermediate Similarity	NPC475271
0.8222	Intermediate Similarity	NPC113626
0.8211	Intermediate Similarity	NPC162730
0.8182	Intermediate Similarity	NPC472116
0.8177	Intermediate Similarity	NPC472108
0.8177	Intermediate Similarity	NPC139291
0.8162	Intermediate Similarity	NPC472097
0.8148	Intermediate Similarity	NPC241024
0.8115	Intermediate Similarity	NPC474116
0.8105	Intermediate Similarity	NPC214428
0.809	Intermediate Similarity	NPC174788
0.8056	Intermediate Similarity	NPC84827
0.8056	Intermediate Similarity	NPC145885
0.8056	Intermediate Similarity	NPC14113
0.8043	Intermediate Similarity	NPC160381
0.8043	Intermediate Similarity	NPC62749
0.804	Intermediate Similarity	NPC305984
0.8032	Intermediate Similarity	NPC57994
0.8032	Intermediate Similarity	NPC289299
0.8021	Intermediate Similarity	NPC472292
0.802	Intermediate Similarity	NPC472098
0.8011	Intermediate Similarity	NPC469470
0.8011	Intermediate Similarity	NPC469501
0.799	Intermediate Similarity	NPC277350
0.7989	Intermediate Similarity	NPC472293
0.7978	Intermediate Similarity	NPC472104
0.7967	Intermediate Similarity	NPC91179
0.7958	Intermediate Similarity	NPC472297
0.7958	Intermediate Similarity	NPC472296
0.7949	Intermediate Similarity	NPC477065
0.7946	Intermediate Similarity	NPC478077
0.7943	Intermediate Similarity	NPC81229
0.7943	Intermediate Similarity	NPC255229
0.7929	Intermediate Similarity	NPC118940
0.791	Intermediate Similarity	NPC96321
0.791	Intermediate Similarity	NPC473041
0.7901	Intermediate Similarity	NPC267885
0.7895	Intermediate Similarity	NPC102592
0.7895	Intermediate Similarity	NPC79356
0.788	Intermediate Similarity	NPC472109
0.788	Intermediate Similarity	NPC472110
0.7857	Intermediate Similarity	NPC474905
0.7849	Intermediate Similarity	NPC235684
0.7846	Intermediate Similarity	NPC132539
0.7845	Intermediate Similarity	NPC149155
0.7845	Intermediate Similarity	NPC203468
0.7845	Intermediate Similarity	NPC329688
0.7845	Intermediate Similarity	NPC110500
0.7845	Intermediate Similarity	NPC189812
0.7844	Intermediate Similarity	NPC88097
0.7842	Intermediate Similarity	NPC474121
0.7839	Intermediate Similarity	NPC264176
0.7828	Intermediate Similarity	NPC471304
0.7826	Intermediate Similarity	NPC311906
0.7821	Intermediate Similarity	NPC78020
0.7814	Intermediate Similarity	NPC248041
0.7814	Intermediate Similarity	NPC126709
0.7812	Intermediate Similarity	NPC67288
0.78	Intermediate Similarity	NPC472291
0.7797	Intermediate Similarity	NPC194881
0.7796	Intermediate Similarity	NPC133003
0.7795	Intermediate Similarity	NPC476098
0.7761	Intermediate Similarity	NPC477979
0.776	Intermediate Similarity	NPC14325
0.776	Intermediate Similarity	NPC111275
0.776	Intermediate Similarity	NPC28848
0.776	Intermediate Similarity	NPC141454
0.774	Intermediate Similarity	NPC33949
0.7723	Intermediate Similarity	NPC469928
0.7723	Intermediate Similarity	NPC330009
0.7719	Intermediate Similarity	NPC470440
0.7717	Intermediate Similarity	NPC283219
0.7717	Intermediate Similarity	NPC213468
0.7705	Intermediate Similarity	NPC472122
0.7705	Intermediate Similarity	NPC24594
0.7704	Intermediate Similarity	NPC476115
0.7704	Intermediate Similarity	NPC165599
0.7692	Intermediate Similarity	NPC478078
0.7688	Intermediate Similarity	NPC159125
0.7688	Intermediate Similarity	NPC470205
0.7685	Intermediate Similarity	NPC312645
0.768	Intermediate Similarity	NPC74413
0.7678	Intermediate Similarity	NPC473105
0.7672	Intermediate Similarity	NPC321708
0.767	Intermediate Similarity	NPC285469
0.7667	Intermediate Similarity	NPC470509
0.7663	Intermediate Similarity	NPC326575
0.766	Intermediate Similarity	NPC135601
0.766	Intermediate Similarity	NPC17273
0.766	Intermediate Similarity	NPC141612
0.7653	Intermediate Similarity	NPC260900
0.765	Intermediate Similarity	NPC234999
0.7647	Intermediate Similarity	NPC281049
0.7647	Intermediate Similarity	NPC228835
0.7641	Intermediate Similarity	NPC249040
0.7641	Intermediate Similarity	NPC329793
0.7634	Intermediate Similarity	NPC71037
0.763	Intermediate Similarity	NPC21605
0.7624	Intermediate Similarity	NPC89508
0.7622	Intermediate Similarity	NPC55772
0.7609	Intermediate Similarity	NPC84347
0.7606	Intermediate Similarity	NPC280290
0.7605	Intermediate Similarity	NPC198988
0.7602	Intermediate Similarity	NPC471944
0.76	Intermediate Similarity	NPC469743
0.76	Intermediate Similarity	NPC478158
0.7594	Intermediate Similarity	NPC19679
0.7592	Intermediate Similarity	NPC138370
0.7588	Intermediate Similarity	NPC53344
0.7581	Intermediate Similarity	NPC472105
0.7581	Intermediate Similarity	NPC187827
0.7576	Intermediate Similarity	NPC475847
0.7576	Intermediate Similarity	NPC185742
0.7574	Intermediate Similarity	NPC475778
0.7566	Intermediate Similarity	NPC315555
0.7561	Intermediate Similarity	NPC303658
0.756	Intermediate Similarity	NPC325252
0.755	Intermediate Similarity	NPC475910
0.7547	Intermediate Similarity	NPC474192
0.7547	Intermediate Similarity	NPC475720
0.7544	Intermediate Similarity	NPC473868
0.7544	Intermediate Similarity	NPC63157
0.7539	Intermediate Similarity	NPC324091
0.7538	Intermediate Similarity	NPC306376
0.7538	Intermediate Similarity	NPC300156
0.7536	Intermediate Similarity	NPC60621
0.7526	Intermediate Similarity	NPC17059
0.7523	Intermediate Similarity	NPC57453
0.7513	Intermediate Similarity	NPC88315
0.75	Intermediate Similarity	NPC478157
0.75	Intermediate Similarity	NPC244741
0.75	Intermediate Similarity	NPC4687
0.75	Intermediate Similarity	NPC16667
0.7488	Intermediate Similarity	NPC184680
0.7487	Intermediate Similarity	NPC227582
0.7487	Intermediate Similarity	NPC473376
0.7486	Intermediate Similarity	NPC475990
0.7486	Intermediate Similarity	NPC474880
0.7486	Intermediate Similarity	NPC221786
0.7485	Intermediate Similarity	NPC59084
0.7475	Intermediate Similarity	NPC137589

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 NPC196251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	505
0.2-0.3	692
0.3-0.4	1348
0.4-0.5	2482
0.5-0.6	2679
0.6-0.7	1088
0.7-0.8	173
0.8-0.85	1
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9435	High Similarity	NPD4501	Approved
0.9435	High Similarity	NPD4500	Approved
0.8696	High Similarity	NPD4600	Approved
0.8696	High Similarity	NPD4601	Approved
0.8407	Intermediate Similarity	NPD4499	Approved
0.8032	Intermediate Similarity	NPD4602	Approved
0.791	Intermediate Similarity	NPD2915	Discontinued
0.7906	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5104	Approved
0.788	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5003	Discontinued
0.7845	Intermediate Similarity	NPD482	Approved
0.7821	Intermediate Similarity	NPD2844	Phase 3
0.7817	Intermediate Similarity	NPD2510	Approved
0.7817	Intermediate Similarity	NPD2509	Approved
0.7811	Intermediate Similarity	NPD3393	Approved
0.7811	Intermediate Similarity	NPD3389	Approved
0.7811	Intermediate Similarity	NPD3394	Approved
0.7802	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2092	Phase 2
0.7784	Intermediate Similarity	NPD2094	Phase 2
0.7784	Intermediate Similarity	NPD2095	Phase 2
0.7778	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2091	Phase 2
0.7742	Intermediate Similarity	NPD2096	Phase 2
0.7716	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6176	Phase 1
0.77	Intermediate Similarity	NPD7470	Discontinued
0.7696	Intermediate Similarity	NPD6770	Approved
0.7692	Intermediate Similarity	NPD750	Phase 2
0.7688	Intermediate Similarity	NPD4506	Discontinued
0.768	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5901	Discontinued
0.7662	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD4885	Approved
0.7606	Intermediate Similarity	NPD5075	Discontinued
0.7581	Intermediate Similarity	NPD5473	Discontinued
0.7563	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD2564	Approved
0.7539	Intermediate Similarity	NPD2565	Phase 2
0.7538	Intermediate Similarity	NPD4397	Phase 1
0.7514	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD4520	Approved
0.75	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6248	Phase 2
0.75	Intermediate Similarity	NPD6249	Phase 2
0.7488	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4334	Discontinued
0.7462	Intermediate Similarity	NPD6479	Discontinued
0.746	Intermediate Similarity	NPD6178	Phase 3
0.7416	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5293	Phase 2
0.74	Intermediate Similarity	NPD3947	Discontinued
0.74	Intermediate Similarity	NPD5426	Phase 3
0.7399	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1534	Approved
0.7391	Intermediate Similarity	NPD5632	Approved
0.7389	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7956	Approved
0.7389	Intermediate Similarity	NPD7955	Approved
0.7383	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD5444	Phase 1
0.7376	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7957	Phase 1
0.7363	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7708	Approved
0.7353	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5913	Phase 3
0.732	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1326	Approved
0.7297	Intermediate Similarity	NPD1325	Approved
0.7297	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7619	Phase 3
0.7296	Intermediate Similarity	NPD7618	Phase 3
0.7291	Intermediate Similarity	NPD5658	Approved
0.7291	Intermediate Similarity	NPD7665	Phase 2
0.7291	Intermediate Similarity	NPD7666	Phase 3
0.7287	Intermediate Similarity	NPD2144	Approved
0.7285	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4315	Phase 2
0.7277	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5065	Approved
0.7268	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5475	Discontinued
0.7264	Intermediate Similarity	NPD8072	Approved
0.7263	Intermediate Similarity	NPD3038	Discontinued
0.7258	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4948	Discontinued
0.7251	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4463	Approved
0.7247	Intermediate Similarity	NPD4462	Approved
0.7246	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5020	Approved
0.7238	Intermediate Similarity	NPD6242	Discontinued
0.7236	Intermediate Similarity	NPD6999	Discontinued
0.7236	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7454	Approved
0.7233	Intermediate Similarity	NPD7455	Approved
0.7231	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7803	Approved
0.7228	Intermediate Similarity	NPD8283	Approved
0.7228	Intermediate Similarity	NPD8282	Approved
0.7228	Intermediate Similarity	NPD8115	Approved
0.7228	Intermediate Similarity	NPD56	Approved
0.7228	Intermediate Similarity	NPD8114	Approved
0.7225	Intermediate Similarity	NPD3319	Phase 1
0.7225	Intermediate Similarity	NPD3318	Approved
0.7225	Intermediate Similarity	NPD3320	Approved
0.7222	Intermediate Similarity	NPD6664	Approved
0.722	Intermediate Similarity	NPD8358	Approved
0.7219	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5897	Approved
0.7211	Intermediate Similarity	NPD5899	Approved
0.7211	Intermediate Similarity	NPD5898	Approved
0.7209	Intermediate Similarity	NPD5479	Discontinued
0.7206	Intermediate Similarity	NPD8399	Phase 1
0.7206	Intermediate Similarity	NPD8423	Phase 2
0.72	Intermediate Similarity	NPD484	Approved
0.7196	Intermediate Similarity	NPD7865	Approved
0.7196	Intermediate Similarity	NPD6164	Phase 2
0.7196	Intermediate Similarity	NPD6165	Phase 2
0.7184	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5487	Phase 1
0.7178	Intermediate Similarity	NPD2920	Discontinued
0.7177	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD1683	Approved
0.7173	Intermediate Similarity	NPD4204	Approved
0.7173	Intermediate Similarity	NPD4203	Approved
0.7172	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2837	Discontinued
0.7157	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5482	Discontinued
0.7151	Intermediate Similarity	NPD3833	Phase 3
0.7151	Intermediate Similarity	NPD3835	Phase 3
0.715	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1722	Approved
0.7143	Intermediate Similarity	NPD4326	Phase 2
0.7143	Intermediate Similarity	NPD2336	Approved
0.7136	Intermediate Similarity	NPD5072	Discontinued
0.7136	Intermediate Similarity	NPD6206	Phase 1
0.7122	Intermediate Similarity	NPD2916	Discontinued
0.7121	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7944	Discontinued
0.712	Intermediate Similarity	NPD6595	Phase 3
0.712	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7404	Approved
0.7107	Intermediate Similarity	NPD5505	Discontinued
0.7104	Intermediate Similarity	NPD2214	Approved
0.7104	Intermediate Similarity	NPD2213	Approved
0.71	Intermediate Similarity	NPD6261	Phase 3
0.7098	Intermediate Similarity	NPD7564	Discontinued
0.7085	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3435	Discontinued
0.7081	Intermediate Similarity	NPD5140	Approved
0.7081	Intermediate Similarity	NPD5138	Approved
0.7079	Intermediate Similarity	NPD7727	Phase 2
0.7079	Intermediate Similarity	NPD7817	Phase 1
0.7068	Intermediate Similarity	NPD4079	Approved
0.7068	Intermediate Similarity	NPD4076	Approved
0.7062	Intermediate Similarity	NPD5254	Discontinued
0.7062	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8272	Phase 2
0.7053	Intermediate Similarity	NPD4075	Phase 2
0.7053	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2880	Discontinued
0.7047	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD8073	Approved
0.7041	Intermediate Similarity	NPD7234	Approved
0.7041	Intermediate Similarity	NPD7233	Approved
0.7037	Intermediate Similarity	NPD7730	Approved
0.7037	Intermediate Similarity	NPD7731	Approved
0.7035	Intermediate Similarity	NPD4558	Phase 2
0.7035	Intermediate Similarity	NPD3385	Approved
0.7033	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7951	Approved
0.7032	Intermediate Similarity	NPD7791	Approved
0.7032	Intermediate Similarity	NPD7953	Approved
0.7032	Intermediate Similarity	NPD7950	Approved
0.7032	Intermediate Similarity	NPD7952	Approved
0.7032	Intermediate Similarity	NPD7789	Approved
0.7032	Intermediate Similarity	NPD7790	Approved
0.703	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD786	Approved
0.7024	Intermediate Similarity	NPD3003	Approved
0.7023	Intermediate Similarity	NPD7271	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