NPASS Compound

Structure

NPC329688 OpenBabel07101718192D 22 26 0 0 1 0 0 0 0 0999 V2000 1.5149 -1.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7493 -1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7493 -2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 -0.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 -2.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8001 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6124 -1.5280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3217 -1.7730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7062 -0.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5840 -2.0371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 -1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0172 -1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0662 -0.8831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1979 -1.4136 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4794 -1.7370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0172 -2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4784 -1.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 -0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0662 -2.5012 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.4349 -3.0259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 13 2 0 0 0 0 5 17 2 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 21 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 1 1 6 0 0 0 11 22 1 0 0 0 0 12 8 1 6 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 11 1 6 0 0 0 15 19 1 0 0 0 0 16 9 1 6 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.19
Volume:	314.636
LogP:	3.026
LogD:	3.084
LogS:	-2.869
# Rotatable Bonds:	1
TPSA:	39.26
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.849
Synthetic Accessibility Score:	5.112
Fsp3:	0.579
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:	-5.207
MDCK Permeability:	6.061630301701371e-06
Pgp-inhibitor:	0.945
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.503
Plasma Protein Binding (PPB):	74.8974380493164%
Volume Distribution (VD):	3.664
Pgp-substrate:	27.519899368286133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.884
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.847
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.747

ADMET: Excretion

Clearance (CL):	6.329
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.669
Human Hepatotoxicity (H-HT):	0.928
Drug-inuced Liver Injury (DILI):	0.801
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.096
Carcinogencity:	0.349
Eye Corrosion:	0.011
Eye Irritation:	0.239
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC329688

Natural Product ID:	NPC329688
*Common Name:**	Heyneanine
IUPAC Name:	n.a.
Synonyms:	Heyneanine
Standard InCHIKey:	TVPHSOXWTLOHCG-CCISYGEFSA-N
Standard InCHI:	InChI=1S/C19H24N2O/c1-11(22)15-8-12-9-16-18-14(6-7-21(10-12)19(15)16)13-4-2-3-5-17(13)20-18/h2-5,11-12,15-16,19-20,22H,6-10H2,1H3/t11-,12-,15-,16-,19-/m0/s1
SMILES:	C[C@@H]([C@@H]1C[C@H]2C[C@H]3c4c(CCN(C2)[C@@H]13)c1ccccc1[nH]4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461609
PubChem CID:	44566758
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-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
NPO32495	tabernaemontana calcarea	Species	Apocynaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[12713407]
NPO6246	Ervatamia hainanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26024020]
NPO6246	Ervatamia hainanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10.7	ug.mL-1	PMID[470642]

☑ 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 NPC329688 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	344
0.1-0.2	1776
0.2-0.3	12617
0.3-0.4	19743
0.4-0.5	3753
0.5-0.6	2310
0.6-0.7	1540
0.7-0.8	542
0.8-0.85	54
0.85-0.9	12
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189812
0.9157	High Similarity	NPC19679
0.8963	High Similarity	NPC472123
0.8896	High Similarity	NPC317430
0.8837	High Similarity	NPC95783
0.8817	High Similarity	NPC139291
0.8817	High Similarity	NPC472108
0.8608	High Similarity	NPC21605
0.8526	High Similarity	NPC473868
0.8526	High Similarity	NPC63157
0.8488	Intermediate Similarity	NPC472109
0.8488	Intermediate Similarity	NPC472110
0.8424	Intermediate Similarity	NPC16667
0.8409	Intermediate Similarity	NPC329858
0.8405	Intermediate Similarity	NPC285469
0.8333	Intermediate Similarity	NPC154293
0.8323	Intermediate Similarity	NPC470508
0.8305	Intermediate Similarity	NPC469470
0.8305	Intermediate Similarity	NPC469501
0.8304	Intermediate Similarity	NPC472122
0.8304	Intermediate Similarity	NPC24594
0.8294	Intermediate Similarity	NPC34508
0.828	Intermediate Similarity	NPC475910
0.8256	Intermediate Similarity	NPC326575
0.8256	Intermediate Similarity	NPC151939
0.8249	Intermediate Similarity	NPC175474
0.8246	Intermediate Similarity	NPC275305
0.8246	Intermediate Similarity	NPC37423
0.8232	Intermediate Similarity	NPC207726
0.8225	Intermediate Similarity	NPC201700
0.8202	Intermediate Similarity	NPC314333
0.8197	Intermediate Similarity	NPC79129
0.8197	Intermediate Similarity	NPC249150
0.8197	Intermediate Similarity	NPC81654
0.8197	Intermediate Similarity	NPC329747
0.8197	Intermediate Similarity	NPC313985
0.8197	Intermediate Similarity	NPC195461
0.8197	Intermediate Similarity	NPC49196
0.8193	Intermediate Similarity	NPC67056
0.8187	Intermediate Similarity	NPC50503
0.8182	Intermediate Similarity	NPC87755
0.8182	Intermediate Similarity	NPC469785
0.8176	Intermediate Similarity	NPC280548
0.8166	Intermediate Similarity	NPC474561
0.8166	Intermediate Similarity	NPC49954
0.8161	Intermediate Similarity	NPC187827
0.8161	Intermediate Similarity	NPC472105
0.8161	Intermediate Similarity	NPC300688
0.816	Intermediate Similarity	NPC33421
0.8155	Intermediate Similarity	NPC311276
0.815	Intermediate Similarity	NPC68354
0.814	Intermediate Similarity	NPC472586
0.8133	Intermediate Similarity	NPC469762
0.8118	Intermediate Similarity	NPC63751
0.8114	Intermediate Similarity	NPC233936
0.8113	Intermediate Similarity	NPC59084
0.8103	Intermediate Similarity	NPC270009
0.8103	Intermediate Similarity	NPC215795
0.8103	Intermediate Similarity	NPC133261
0.8103	Intermediate Similarity	NPC472443
0.8103	Intermediate Similarity	NPC176199
0.8095	Intermediate Similarity	NPC475422
0.8092	Intermediate Similarity	NPC121903
0.8084	Intermediate Similarity	NPC230869
0.8081	Intermediate Similarity	NPC97525
0.807	Intermediate Similarity	NPC194411
0.8061	Intermediate Similarity	NPC259644
0.8061	Intermediate Similarity	NPC469763
0.8061	Intermediate Similarity	NPC469760
0.8061	Intermediate Similarity	NPC469786
0.8061	Intermediate Similarity	NPC25008
0.8061	Intermediate Similarity	NPC73952
0.8061	Intermediate Similarity	NPC469765
0.8059	Intermediate Similarity	NPC160105
0.8059	Intermediate Similarity	NPC54988
0.8057	Intermediate Similarity	NPC15840
0.8047	Intermediate Similarity	NPC40779
0.8034	Intermediate Similarity	NPC474707
0.8023	Intermediate Similarity	NPC472294
0.8012	Intermediate Similarity	NPC70922
0.8012	Intermediate Similarity	NPC80597
0.8012	Intermediate Similarity	NPC212376
0.8012	Intermediate Similarity	NPC211572
0.8012	Intermediate Similarity	NPC75540
0.8012	Intermediate Similarity	NPC470507
0.8011	Intermediate Similarity	NPC162730
0.8011	Intermediate Similarity	NPC113626
0.8011	Intermediate Similarity	NPC192270
0.8	Intermediate Similarity	NPC472112
0.8	Intermediate Similarity	NPC329793
0.8	Intermediate Similarity	NPC249040
0.7989	Intermediate Similarity	NPC317030
0.7989	Intermediate Similarity	NPC52557
0.7989	Intermediate Similarity	NPC204565
0.7988	Intermediate Similarity	NPC282231
0.7977	Intermediate Similarity	NPC314603
0.7967	Intermediate Similarity	NPC474177
0.7966	Intermediate Similarity	NPC472444
0.7944	Intermediate Similarity	NPC173028
0.7944	Intermediate Similarity	NPC65215
0.7941	Intermediate Similarity	NPC194640
0.7937	Intermediate Similarity	NPC88097
0.7935	Intermediate Similarity	NPC232130
0.7929	Intermediate Similarity	NPC279918
0.7929	Intermediate Similarity	NPC81229
0.7929	Intermediate Similarity	NPC255229
0.7914	Intermediate Similarity	NPC474116
0.7912	Intermediate Similarity	NPC472113
0.7911	Intermediate Similarity	NPC198988
0.7904	Intermediate Similarity	NPC38736
0.7888	Intermediate Similarity	NPC2949
0.7887	Intermediate Similarity	NPC469928
0.7887	Intermediate Similarity	NPC330009
0.7879	Intermediate Similarity	NPC37548
0.7876	Intermediate Similarity	NPC478074
0.787	Intermediate Similarity	NPC56765
0.7862	Intermediate Similarity	NPC325252
0.7857	Intermediate Similarity	NPC141353
0.7857	Intermediate Similarity	NPC243716
0.7853	Intermediate Similarity	NPC198339
0.7845	Intermediate Similarity	NPC102338
0.7845	Intermediate Similarity	NPC63199
0.7845	Intermediate Similarity	NPC196251
0.7845	Intermediate Similarity	NPC111602
0.7841	Intermediate Similarity	NPC293472
0.7841	Intermediate Similarity	NPC59269
0.7836	Intermediate Similarity	NPC271797
0.7836	Intermediate Similarity	NPC21174
0.7826	Intermediate Similarity	NPC133366
0.7812	Intermediate Similarity	NPC126066
0.7811	Intermediate Similarity	NPC129721
0.7809	Intermediate Similarity	NPC314394
0.7809	Intermediate Similarity	NPC302191
0.7805	Intermediate Similarity	NPC314372
0.7805	Intermediate Similarity	NPC470440
0.7801	Intermediate Similarity	NPC314957
0.7797	Intermediate Similarity	NPC219336
0.779	Intermediate Similarity	NPC472323
0.7784	Intermediate Similarity	NPC288785
0.7778	Intermediate Similarity	NPC15102
0.7771	Intermediate Similarity	NPC187951
0.7765	Intermediate Similarity	NPC163055
0.7749	Intermediate Similarity	NPC477065
0.7742	Intermediate Similarity	NPC229332
0.774	Intermediate Similarity	NPC183662
0.774	Intermediate Similarity	NPC15573
0.774	Intermediate Similarity	NPC217372
0.774	Intermediate Similarity	NPC234987
0.7733	Intermediate Similarity	NPC102423
0.7732	Intermediate Similarity	NPC475778
0.7722	Intermediate Similarity	NPC475450
0.7722	Intermediate Similarity	NPC165201
0.772	Intermediate Similarity	NPC471304
0.772	Intermediate Similarity	NPC234999
0.7714	Intermediate Similarity	NPC158129
0.7713	Intermediate Similarity	NPC199851
0.7713	Intermediate Similarity	NPC312870
0.7713	Intermediate Similarity	NPC294909
0.7713	Intermediate Similarity	NPC128265
0.7713	Intermediate Similarity	NPC254240
0.7692	Intermediate Similarity	NPC475602
0.7692	Intermediate Similarity	NPC119700
0.7688	Intermediate Similarity	NPC231342
0.7683	Intermediate Similarity	NPC190296
0.768	Intermediate Similarity	NPC163421
0.768	Intermediate Similarity	NPC188387
0.767	Intermediate Similarity	NPC313791
0.7668	Intermediate Similarity	NPC476116
0.7667	Intermediate Similarity	NPC472104
0.7665	Intermediate Similarity	NPC124005
0.7661	Intermediate Similarity	NPC475990
0.7661	Intermediate Similarity	NPC474880
0.7661	Intermediate Similarity	NPC221786
0.7661	Intermediate Similarity	NPC318065
0.7661	Intermediate Similarity	NPC206819
0.766	Intermediate Similarity	NPC241024
0.7658	Intermediate Similarity	NPC475428
0.7658	Intermediate Similarity	NPC22079
0.7654	Intermediate Similarity	NPC469896
0.765	Intermediate Similarity	NPC46413
0.7644	Intermediate Similarity	NPC109447
0.764	Intermediate Similarity	NPC248454
0.7636	Intermediate Similarity	NPC242556
0.7634	Intermediate Similarity	NPC220151
0.7634	Intermediate Similarity	NPC19692
0.7624	Intermediate Similarity	NPC190007
0.7622	Intermediate Similarity	NPC55493
0.7619	Intermediate Similarity	NPC24678
0.7619	Intermediate Similarity	NPC105818
0.7616	Intermediate Similarity	NPC473320
0.7616	Intermediate Similarity	NPC131718
0.7616	Intermediate Similarity	NPC229173
0.7614	Intermediate Similarity	NPC6982
0.761	Intermediate Similarity	NPC475720
0.761	Intermediate Similarity	NPC474192
0.761	Intermediate Similarity	NPC179365
0.7606	Intermediate Similarity	NPC265576
0.76	Intermediate Similarity	NPC471506
0.7598	Intermediate Similarity	NPC72980
0.7598	Intermediate Similarity	NPC213468

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 NPC329688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	544
0.2-0.3	756
0.3-0.4	1651
0.4-0.5	2702
0.5-0.6	2320
0.6-0.7	842
0.7-0.8	134
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1326	Approved
0.8284	Intermediate Similarity	NPD1325	Approved
0.8208	Intermediate Similarity	NPD4076	Approved
0.8208	Intermediate Similarity	NPD4079	Approved
0.8202	Intermediate Similarity	NPD4499	Approved
0.8197	Intermediate Similarity	NPD4601	Approved
0.8197	Intermediate Similarity	NPD4600	Approved
0.815	Intermediate Similarity	NPD3506	Approved
0.815	Intermediate Similarity	NPD3505	Approved
0.8142	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5065	Approved
0.8092	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6595	Phase 3
0.7943	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD8386	Phase 2
0.7865	Intermediate Similarity	NPD5596	Phase 2
0.7853	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD2144	Approved
0.7831	Intermediate Similarity	NPD4463	Approved
0.7831	Intermediate Similarity	NPD4462	Approved
0.7816	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD3038	Discontinued
0.7803	Intermediate Similarity	NPD4639	Approved
0.7803	Intermediate Similarity	NPD4638	Approved
0.7803	Intermediate Similarity	NPD5021	Discontinued
0.7803	Intermediate Similarity	NPD4640	Approved
0.7784	Intermediate Similarity	NPD2882	Phase 1
0.7784	Intermediate Similarity	NPD2381	Approved
0.7784	Intermediate Similarity	NPD2382	Approved
0.7784	Intermediate Similarity	NPD2380	Approved
0.7778	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD1683	Approved
0.7744	Intermediate Similarity	NPD5254	Discontinued
0.774	Intermediate Similarity	NPD4181	Approved
0.7736	Intermediate Similarity	NPD3385	Approved
0.7733	Intermediate Similarity	NPD3323	Discontinued
0.7713	Intermediate Similarity	NPD4501	Approved
0.7713	Intermediate Similarity	NPD4500	Approved
0.7692	Intermediate Similarity	NPD8431	Approved
0.7674	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD5913	Phase 3
0.7654	Intermediate Similarity	NPD5473	Discontinued
0.765	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1722	Approved
0.7622	Intermediate Similarity	NPD3404	Approved
0.76	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD2383	Phase 1
0.7584	Intermediate Similarity	NPD4075	Phase 2
0.7574	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6158	Phase 2
0.7569	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3100	Discontinued
0.7529	Intermediate Similarity	NPD2837	Discontinued
0.7529	Intermediate Similarity	NPD5140	Approved
0.7529	Intermediate Similarity	NPD5138	Approved
0.7528	Intermediate Similarity	NPD4128	Approved
0.7515	Intermediate Similarity	NPD1592	Phase 3
0.7514	Intermediate Similarity	NPD3610	Approved
0.7514	Intermediate Similarity	NPD3609	Approved
0.7513	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7957	Phase 1
0.75	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD786	Approved
0.75	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4703	Approved
0.75	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4702	Approved
0.7436	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD482	Approved
0.7423	Intermediate Similarity	NPD3003	Approved
0.7419	Intermediate Similarity	NPD6281	Approved
0.7405	Intermediate Similarity	NPD3961	Discontinued
0.7401	Intermediate Similarity	NPD2641	Approved
0.7401	Intermediate Similarity	NPD2640	Approved
0.7398	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2095	Phase 2
0.7377	Intermediate Similarity	NPD2092	Phase 2
0.7377	Intermediate Similarity	NPD2094	Phase 2
0.7375	Intermediate Similarity	NPD3654	Approved
0.7371	Intermediate Similarity	NPD5426	Phase 3
0.7368	Intermediate Similarity	NPD5003	Discontinued
0.7353	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2091	Phase 2
0.7337	Intermediate Similarity	NPD2096	Phase 2
0.733	Intermediate Similarity	NPD6978	Phase 2
0.733	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8072	Approved
0.7317	Intermediate Similarity	NPD1254	Approved
0.7317	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1253	Approved
0.7317	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1256	Approved
0.7317	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1255	Approved
0.7316	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2172	Phase 1
0.7306	Intermediate Similarity	NPD4511	Phase 1
0.7303	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4326	Phase 2
0.7296	Intermediate Similarity	NPD8322	Phase 2
0.7294	Intermediate Similarity	NPD4547	Phase 3
0.7282	Intermediate Similarity	NPD8272	Phase 2
0.7278	Intermediate Similarity	NPD750	Phase 2
0.7277	Intermediate Similarity	NPD7948	Phase 1
0.7277	Intermediate Similarity	NPD6664	Approved
0.7273	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5899	Approved
0.7268	Intermediate Similarity	NPD5897	Approved
0.7268	Intermediate Similarity	NPD5898	Approved
0.7263	Intermediate Similarity	NPD7944	Discontinued
0.7253	Intermediate Similarity	NPD8122	Approved
0.7253	Intermediate Similarity	NPD8123	Approved
0.7238	Intermediate Similarity	NPD6492	Phase 2
0.7236	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7935	Phase 2
0.7225	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7817	Phase 1
0.7208	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5862	Discovery
0.7207	Intermediate Similarity	NPD2844	Phase 3
0.7202	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3814	Phase 1
0.7202	Intermediate Similarity	NPD1768	Approved
0.72	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD8115	Approved
0.7194	Intermediate Similarity	NPD5901	Discontinued
0.7194	Intermediate Similarity	NPD8114	Approved
0.7189	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8073	Approved
0.7178	Intermediate Similarity	NPD1251	Discontinued
0.7174	Intermediate Similarity	NPD6452	Discontinued
0.7173	Intermediate Similarity	NPD7619	Phase 3
0.7173	Intermediate Similarity	NPD4602	Approved
0.7173	Intermediate Similarity	NPD7618	Phase 3
0.7172	Intermediate Similarity	NPD5658	Approved
0.7169	Intermediate Similarity	NPD6554	Approved
0.7169	Intermediate Similarity	NPD1262	Discovery
0.7169	Intermediate Similarity	NPD45	Approved
0.716	Intermediate Similarity	NPD947	Approved
0.716	Intermediate Similarity	NPD3717	Discontinued
0.7157	Intermediate Similarity	NPD7194	Discontinued
0.7151	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4957	Phase 2
0.715	Intermediate Similarity	NPD7271	Approved
0.715	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2928	Phase 2
0.7143	Intermediate Similarity	NPD2150	Discontinued
0.7143	Intermediate Similarity	NPD6026	Approved
0.7143	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5903	Approved
0.7129	Intermediate Similarity	NPD5902	Approved
0.7127	Intermediate Similarity	NPD3116	Approved
0.7127	Intermediate Similarity	NPD3117	Approved
0.7121	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD802	Phase 2
0.7119	Intermediate Similarity	NPD1403	Approved
0.7119	Intermediate Similarity	NPD1404	Approved
0.7114	Intermediate Similarity	NPD3330	Phase 1
0.7113	Intermediate Similarity	NPD2177	Approved
0.7113	Intermediate Similarity	NPD6248	Phase 2
0.7113	Intermediate Similarity	NPD6249	Phase 2
0.7113	Intermediate Similarity	NPD2175	Phase 3
0.7113	Intermediate Similarity	NPD2176	Approved
0.7112	Intermediate Similarity	NPD6227	Discontinued
0.7112	Intermediate Similarity	NPD5555	Phase 1
0.7112	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3835	Phase 3
0.711	Intermediate Similarity	NPD3833	Phase 3
0.7104	Intermediate Similarity	NPD5100	Phase 3
0.7101	Intermediate Similarity	NPD6301	Phase 2
0.709	Intermediate Similarity	NPD4334	Discontinued
0.7088	Intermediate Similarity	NPD7418	Discontinued
0.7085	Intermediate Similarity	NPD2916	Discontinued
0.7081	Intermediate Similarity	NPD7730	Approved
0.7081	Intermediate Similarity	NPD7731	Approved
0.7079	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1684	Approved
0.7079	Intermediate Similarity	NPD1685	Approved
0.7079	Intermediate Similarity	NPD5315	Discontinued
0.7074	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7474	Suspended

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