NPASS Compound

Structure

CID57994 OpenBabel06191715392D 26 30 0 0 1 0 0 0 0 0999 V2000 2.9338 1.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2279 -2.3654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3131 0.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3391 0.9650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3393 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1592 2.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5044 1.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5048 -0.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8341 2.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2146 1.4692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5455 2.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 2.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6696 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6695 0.9646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6696 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8354 1.4461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8349 -1.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6698 0.9640 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8350 -0.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8356 2.4099 0.0000 N 0 0 3 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 0.3039 -2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6513 -0.9534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7969 -1.5035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 3 1 6 0 0 0 21 23 1 0 0 0 0 21 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.19
Volume:	364.172
LogP:	3.548
LogD:	3.464
LogS:	-3.212
# Rotatable Bonds:	3
TPSA:	54.7
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.843
Synthetic Accessibility Score:	3.926
Fsp3:	0.571
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:	-5.06
MDCK Permeability:	1.8073862520395778e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	86.72307586669922%
Volume Distribution (VD):	2.762
Pgp-substrate:	9.232684135437012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.687
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.163
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.648
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	11.017
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.564
Drug-inuced Liver Injury (DILI):	0.151
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.098
Carcinogencity:	0.967
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.392

Download Data

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

Natural Product: NPC57994

Natural Product ID:	NPC57994
*Common Name:**	RXPRRQLKFXBCSJ-HLAWJBBLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RXPRRQLKFXBCSJ-HLAWJBBLSA-N
Standard InCHI:	InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/p+1/t18-,20+,21-/m1/s1
SMILES:	CC[C@]12CCC[NH+]3CCc4c5ccccc5n(c4[C@H]23)[C@@](C1)(C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1728279
PubChem CID:	637570
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002671] Eburnan-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
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	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
Others	4
Potency	3

Activity Type	# Activity
Individual Protein	2
Organism	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	707.9	nM	PMID[568781]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[568781]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[568781]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-6.05	%	PMID[568782]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	18.55	%	PMID[568783]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.12	%	PMID[568784]

☑ 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 NPC57994 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	246
0.1-0.2	1243
0.2-0.3	7553
0.3-0.4	23268
0.4-0.5	4983
0.5-0.6	2849
0.6-0.7	2157
0.7-0.8	339
0.8-0.85	45
0.85-0.9	8
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289299
0.9195	High Similarity	NPC143533
0.9011	High Similarity	NPC469736
0.875	High Similarity	NPC472116
0.8722	High Similarity	NPC478077
0.8596	High Similarity	NPC133261
0.847	Intermediate Similarity	NPC472323
0.8457	Intermediate Similarity	NPC52557
0.8444	Intermediate Similarity	NPC15840
0.8407	Intermediate Similarity	NPC472119
0.8343	Intermediate Similarity	NPC469896
0.8333	Intermediate Similarity	NPC81229
0.8333	Intermediate Similarity	NPC255229
0.8324	Intermediate Similarity	NPC175474
0.8287	Intermediate Similarity	NPC219336
0.8261	Intermediate Similarity	NPC472107
0.8261	Intermediate Similarity	NPC79062
0.8232	Intermediate Similarity	NPC217372
0.8232	Intermediate Similarity	NPC183662
0.8232	Intermediate Similarity	NPC15573
0.8207	Intermediate Similarity	NPC258480
0.8182	Intermediate Similarity	NPC194881
0.8138	Intermediate Similarity	NPC472097
0.8118	Intermediate Similarity	NPC66210
0.8083	Intermediate Similarity	NPC195461
0.8083	Intermediate Similarity	NPC249150
0.8083	Intermediate Similarity	NPC81654
0.8083	Intermediate Similarity	NPC313985
0.8083	Intermediate Similarity	NPC79129
0.8083	Intermediate Similarity	NPC49196
0.8063	Intermediate Similarity	NPC245916
0.8054	Intermediate Similarity	NPC472104
0.8032	Intermediate Similarity	NPC102338
0.8032	Intermediate Similarity	NPC111602
0.8032	Intermediate Similarity	NPC196251
0.8032	Intermediate Similarity	NPC63199
0.8	Intermediate Similarity	NPC113626
0.7979	Intermediate Similarity	NPC50503
0.7978	Intermediate Similarity	NPC24594
0.7978	Intermediate Similarity	NPC472122
0.7957	Intermediate Similarity	NPC159125
0.7946	Intermediate Similarity	NPC472105
0.7946	Intermediate Similarity	NPC187827
0.7935	Intermediate Similarity	NPC234987
0.7895	Intermediate Similarity	NPC472112
0.7812	Intermediate Similarity	NPC472113
0.7806	Intermediate Similarity	NPC254240
0.7806	Intermediate Similarity	NPC128265
0.7806	Intermediate Similarity	NPC312870
0.7806	Intermediate Similarity	NPC199851
0.7806	Intermediate Similarity	NPC294909
0.7796	Intermediate Similarity	NPC248462
0.7795	Intermediate Similarity	NPC149708
0.7772	Intermediate Similarity	NPC472123
0.7767	Intermediate Similarity	NPC52254
0.7766	Intermediate Similarity	NPC472109
0.7766	Intermediate Similarity	NPC472110
0.7742	Intermediate Similarity	NPC326575
0.7703	Intermediate Similarity	NPC475271
0.7672	Intermediate Similarity	NPC139291
0.7672	Intermediate Similarity	NPC472108
0.7668	Intermediate Similarity	NPC473763
0.7668	Intermediate Similarity	NPC117244
0.766	Intermediate Similarity	NPC91179
0.765	Intermediate Similarity	NPC472115
0.765	Intermediate Similarity	NPC472114
0.7641	Intermediate Similarity	NPC220151
0.7641	Intermediate Similarity	NPC19692
0.7637	Intermediate Similarity	NPC271797
0.7637	Intermediate Similarity	NPC21174
0.7634	Intermediate Similarity	NPC469938
0.7617	Intermediate Similarity	NPC314333
0.7617	Intermediate Similarity	NPC329858
0.7612	Intermediate Similarity	NPC238457
0.7609	Intermediate Similarity	NPC317430
0.7606	Intermediate Similarity	NPC126709
0.7606	Intermediate Similarity	NPC248041
0.76	Intermediate Similarity	NPC476098
0.759	Intermediate Similarity	NPC472295
0.759	Intermediate Similarity	NPC247735
0.759	Intermediate Similarity	NPC269886
0.759	Intermediate Similarity	NPC472210
0.759	Intermediate Similarity	NPC81802
0.7581	Intermediate Similarity	NPC161861
0.7553	Intermediate Similarity	NPC145885
0.7553	Intermediate Similarity	NPC14113
0.7553	Intermediate Similarity	NPC84827
0.7552	Intermediate Similarity	NPC235684
0.7552	Intermediate Similarity	NPC62749
0.755	Intermediate Similarity	NPC57398
0.7548	Intermediate Similarity	NPC174788
0.7548	Intermediate Similarity	NPC82070
0.7548	Intermediate Similarity	NPC281049
0.7541	Intermediate Similarity	NPC469541
0.7536	Intermediate Similarity	NPC476114
0.7526	Intermediate Similarity	NPC469501
0.7526	Intermediate Similarity	NPC469470
0.7513	Intermediate Similarity	NPC283219
0.75	Intermediate Similarity	NPC134586
0.75	Intermediate Similarity	NPC267885
0.7487	Intermediate Similarity	NPC129909
0.7477	Intermediate Similarity	NPC184680
0.7476	Intermediate Similarity	NPC472098
0.7463	Intermediate Similarity	NPC162730
0.7463	Intermediate Similarity	NPC234999
0.7461	Intermediate Similarity	NPC315555
0.746	Intermediate Similarity	NPC211997
0.745	Intermediate Similarity	NPC214428
0.7448	Intermediate Similarity	NPC470003
0.7447	Intermediate Similarity	NPC203468
0.7447	Intermediate Similarity	NPC110500
0.7447	Intermediate Similarity	NPC149155
0.7443	Intermediate Similarity	NPC470785
0.7433	Intermediate Similarity	NPC158129
0.7418	Intermediate Similarity	NPC129721
0.7416	Intermediate Similarity	NPC312645
0.7415	Intermediate Similarity	NPC478158
0.7402	Intermediate Similarity	NPC53344
0.7395	Intermediate Similarity	NPC33949
0.7394	Intermediate Similarity	NPC477976
0.7393	Intermediate Similarity	NPC472099
0.7391	Intermediate Similarity	NPC475778
0.7386	Intermediate Similarity	NPC20144
0.7376	Intermediate Similarity	NPC474116
0.7368	Intermediate Similarity	NPC64436
0.7364	Intermediate Similarity	NPC474183
0.7363	Intermediate Similarity	NPC285469
0.736	Intermediate Similarity	NPC55493
0.7356	Intermediate Similarity	NPC89508
0.7356	Intermediate Similarity	NPC234078
0.7356	Intermediate Similarity	NPC221100
0.7356	Intermediate Similarity	NPC472291
0.7353	Intermediate Similarity	NPC277350
0.7348	Intermediate Similarity	NPC478076
0.733	Intermediate Similarity	NPC55772
0.7321	Intermediate Similarity	NPC478157
0.732	Intermediate Similarity	NPC62510
0.7317	Intermediate Similarity	NPC244741
0.7313	Intermediate Similarity	NPC241024
0.7306	Intermediate Similarity	NPC469358
0.73	Intermediate Similarity	NPC141454
0.7296	Intermediate Similarity	NPC321708
0.7296	Intermediate Similarity	NPC61435
0.7291	Intermediate Similarity	NPC476874
0.7286	Intermediate Similarity	NPC148183
0.7286	Intermediate Similarity	NPC469928
0.7286	Intermediate Similarity	NPC152768
0.7285	Intermediate Similarity	NPC470784
0.7282	Intermediate Similarity	NPC311858
0.7277	Intermediate Similarity	NPC111275
0.7273	Intermediate Similarity	NPC472292
0.7268	Intermediate Similarity	NPC228835
0.7255	Intermediate Similarity	NPC165599
0.7246	Intermediate Similarity	NPC469743
0.7245	Intermediate Similarity	NPC17059
0.724	Intermediate Similarity	NPC213468
0.7234	Intermediate Similarity	NPC78020
0.7228	Intermediate Similarity	NPC192674
0.7225	Intermediate Similarity	NPC203754
0.7225	Intermediate Similarity	NPC264176
0.7225	Intermediate Similarity	NPC121903
0.7225	Intermediate Similarity	NPC476441
0.7225	Intermediate Similarity	NPC150048
0.7217	Intermediate Similarity	NPC473310
0.7216	Intermediate Similarity	NPC472444
0.7216	Intermediate Similarity	NPC104483
0.7214	Intermediate Similarity	NPC262898
0.7213	Intermediate Similarity	NPC207726
0.7204	Intermediate Similarity	NPC16667
0.7204	Intermediate Similarity	NPC330009
0.7202	Intermediate Similarity	NPC477175
0.7202	Intermediate Similarity	NPC470730
0.7194	Intermediate Similarity	NPC94752
0.7192	Intermediate Similarity	NPC249040
0.719	Intermediate Similarity	NPC54744
0.719	Intermediate Similarity	NPC317752
0.7184	Intermediate Similarity	NPC317373
0.7181	Intermediate Similarity	NPC56233
0.7179	Intermediate Similarity	NPC472294
0.7178	Intermediate Similarity	NPC470499
0.7173	Intermediate Similarity	NPC472586
0.7173	Intermediate Similarity	NPC189812
0.7173	Intermediate Similarity	NPC329688
0.7169	Intermediate Similarity	NPC475969
0.7169	Intermediate Similarity	NPC475859
0.7164	Intermediate Similarity	NPC472293
0.7164	Intermediate Similarity	NPC179701
0.7163	Intermediate Similarity	NPC469589
0.7156	Intermediate Similarity	NPC313640
0.715	Intermediate Similarity	NPC11126
0.715	Intermediate Similarity	NPC472443
0.715	Intermediate Similarity	NPC477065
0.7143	Intermediate Similarity	NPC207020
0.7143	Intermediate Similarity	NPC81535
0.7143	Intermediate Similarity	NPC318299
0.7136	Intermediate Similarity	NPC132539
0.7136	Intermediate Similarity	NPC473376
0.7136	Intermediate Similarity	NPC327592
0.7136	Intermediate Similarity	NPC165743
0.7135	Intermediate Similarity	NPC84347

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 NPC57994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	423
0.2-0.3	666
0.3-0.4	1651
0.4-0.5	2541
0.5-0.6	2705
0.6-0.7	877
0.7-0.8	116
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4602	Approved
0.9297	High Similarity	NPD4520	Approved
0.8083	Intermediate Similarity	NPD4601	Approved
0.8083	Intermediate Similarity	NPD4600	Approved
0.7978	Intermediate Similarity	NPD5104	Approved
0.7908	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5075	Discontinued
0.7811	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4501	Approved
0.7806	Intermediate Similarity	NPD4500	Approved
0.7795	Intermediate Similarity	NPD4397	Phase 1
0.779	Intermediate Similarity	NPD2915	Discontinued
0.7772	Intermediate Similarity	NPD750	Phase 2
0.7766	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD4499	Approved
0.7612	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4326	Phase 2
0.7576	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2094	Phase 2
0.7487	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2095	Phase 2
0.7487	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2092	Phase 2
0.7475	Intermediate Similarity	NPD6987	Phase 1
0.7462	Intermediate Similarity	NPD7944	Discontinued
0.7451	Intermediate Similarity	NPD7665	Phase 2
0.7451	Intermediate Similarity	NPD7666	Phase 3
0.7448	Intermediate Similarity	NPD2096	Phase 2
0.7448	Intermediate Similarity	NPD7483	Phase 2
0.7448	Intermediate Similarity	NPD2091	Phase 2
0.7448	Intermediate Similarity	NPD7482	Phase 2
0.7447	Intermediate Similarity	NPD482	Approved
0.7435	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6249	Phase 2
0.74	Intermediate Similarity	NPD6248	Phase 2
0.7396	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6206	Phase 1
0.7382	Intermediate Similarity	NPD6452	Discontinued
0.7354	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6261	Phase 3
0.73	Intermediate Similarity	NPD5003	Discontinued
0.7296	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5899	Approved
0.7292	Intermediate Similarity	NPD5898	Approved
0.7292	Intermediate Similarity	NPD5897	Approved
0.7282	Intermediate Similarity	NPD5809	Phase 3
0.7282	Intermediate Similarity	NPD5444	Phase 1
0.7281	Intermediate Similarity	NPD7824	Approved
0.7273	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7568	Phase 1
0.7268	Intermediate Similarity	NPD7001	Phase 3
0.7255	Intermediate Similarity	NPD5487	Phase 1
0.7234	Intermediate Similarity	NPD2844	Phase 3
0.7228	Intermediate Similarity	NPD6999	Discontinued
0.7228	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7103	Approved
0.7216	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4334	Discontinued
0.72	Intermediate Similarity	NPD4427	Phase 2
0.7189	Intermediate Similarity	NPD7730	Approved
0.7189	Intermediate Similarity	NPD7731	Approved
0.7184	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7790	Approved
0.7182	Intermediate Similarity	NPD7952	Approved
0.7182	Intermediate Similarity	NPD7950	Approved
0.7182	Intermediate Similarity	NPD7791	Approved
0.7182	Intermediate Similarity	NPD7953	Approved
0.7182	Intermediate Similarity	NPD7789	Approved
0.7182	Intermediate Similarity	NPD7951	Approved
0.7181	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6178	Phase 3
0.7176	Intermediate Similarity	NPD7271	Approved
0.7172	Intermediate Similarity	NPD2565	Phase 2
0.7172	Intermediate Similarity	NPD2564	Approved
0.7166	Intermediate Similarity	NPD1631	Approved
0.7156	Intermediate Similarity	NPD4897	Phase 2
0.7143	Intermediate Similarity	NPD6227	Discontinued
0.7136	Intermediate Similarity	NPD8114	Approved
0.7136	Intermediate Similarity	NPD8115	Approved
0.7135	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7618	Phase 3
0.7114	Intermediate Similarity	NPD7619	Phase 3
0.7109	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1575	Approved
0.7105	Intermediate Similarity	NPD1573	Approved
0.7094	Intermediate Similarity	NPD7778	Approved
0.7094	Intermediate Similarity	NPD7777	Approved
0.7094	Intermediate Similarity	NPD53	Approved
0.7068	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7796	Approved
0.7059	Intermediate Similarity	NPD4885	Approved
0.7059	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7797	Approved
0.705	Intermediate Similarity	NPD2336	Approved
0.7048	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3394	Approved
0.7042	Intermediate Similarity	NPD3389	Approved
0.7042	Intermediate Similarity	NPD3393	Approved
0.7037	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7234	Approved
0.7035	Intermediate Similarity	NPD7233	Approved
0.7033	Intermediate Similarity	NPD2916	Discontinued
0.7019	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4315	Phase 2
0.7015	Intermediate Similarity	NPD5505	Discontinued
0.7014	Intermediate Similarity	NPD7470	Discontinued
0.7011	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6158	Phase 2
0.7011	Intermediate Similarity	NPD2882	Phase 1
0.7009	Intermediate Similarity	NPD8325	Phase 3
0.7009	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8326	Phase 3
0.7005	Intermediate Similarity	NPD3777	Phase 3
0.7005	Intermediate Similarity	NPD1630	Approved
0.699	Remote Similarity	NPD7727	Phase 2
0.6986	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2383	Phase 1
0.6985	Remote Similarity	NPD4948	Discontinued
0.6971	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5426	Phase 3
0.6968	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5862	Discovery
0.6959	Remote Similarity	NPD5506	Approved
0.6959	Remote Similarity	NPD5507	Approved
0.6944	Remote Similarity	NPD5020	Approved
0.6938	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7957	Phase 1
0.6934	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3385	Approved
0.6931	Remote Similarity	NPD6665	Discontinued
0.6927	Remote Similarity	NPD8356	Approved
0.6927	Remote Similarity	NPD6846	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7780	Approved
0.6923	Remote Similarity	NPD7781	Approved
0.6915	Remote Similarity	NPD7599	Phase 2
0.6915	Remote Similarity	NPD5255	Approved
0.6912	Remote Similarity	NPD2307	Discontinued
0.6908	Remote Similarity	NPD5017	Discontinued
0.6908	Remote Similarity	NPD7817	Phase 1
0.6906	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7573	Discontinued
0.69	Remote Similarity	NPD3390	Phase 2
0.69	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7716	Approved
0.6895	Remote Similarity	NPD7717	Approved
0.689	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5901	Discontinued
0.6888	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6716	Phase 1
0.6881	Remote Similarity	NPD4918	Discontinued
0.6878	Remote Similarity	NPD8430	Approved
0.6878	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4373	Phase 2
0.6872	Remote Similarity	NPD2380	Approved
0.6872	Remote Similarity	NPD2382	Approved
0.6872	Remote Similarity	NPD2381	Approved
0.6872	Remote Similarity	NPD2896	Discontinued
0.6872	Remote Similarity	NPD5471	Phase 3
0.6866	Remote Similarity	NPD7168	Phase 3
0.6861	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5043	Discontinued
0.686	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.686	Remote Similarity	NPD484	Approved
0.686	Remote Similarity	NPD5427	Suspended
0.6856	Remote Similarity	NPD43	Approved
0.6856	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6182	Approved
0.6854	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4702	Approved
0.6848	Remote Similarity	NPD4703	Approved
0.6845	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2920	Discontinued
0.684	Remote Similarity	NPD5834	Phase 3
0.684	Remote Similarity	NPD5835	Phase 3
0.6838	Remote Similarity	NPD8463	Approved
0.6837	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8122	Approved
0.6837	Remote Similarity	NPD8123	Approved
0.6829	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5512	Phase 3
0.6825	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7222	Phase 2
0.6822	Remote Similarity	NPD7455	Approved
0.6822	Remote Similarity	NPD7454	Approved
0.6821	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6578	Clinical (unspecified phase)

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