NPASS Compound

Structure

NPC470481 OpenBabel07101718232D 28 31 0 0 1 0 0 0 0 0999 V2000 -3.2458 1.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5537 -2.8140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0914 1.7484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2374 -0.1747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2458 0.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2722 1.1455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2041 1.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0986 -0.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2531 0.6955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0986 0.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8941 1.0655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 -1.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1807 -2.1177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6229 -0.9370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6229 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8911 0.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7548 0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4419 -0.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3737 -0.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 0.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6229 0.9370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8911 -1.2265 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0972 -2.3125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9245 -1.1286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 2.3425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6867 0.5834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 28 1 0 0 0 0 5 15 2 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 23 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 13 25 2 0 0 0 0 14 8 1 6 0 0 0 14 15 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 28 1 0 0 0 0 18 22 1 1 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 27 2 0 0 0 0 22 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.2
Volume:	396.178
LogP:	1.608
LogD:	1.465
LogS:	-2.818
# Rotatable Bonds:	2
TPSA:	70.08
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	5.788
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.671
MDCK Permeability:	1.83856172952801e-05
Pgp-inhibitor:	0.902
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.401
30% Bioavailability (F30%):	0.186

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	57.96366500854492%
Volume Distribution (VD):	2.373
Pgp-substrate:	68.0494155883789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.498
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.6
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.942

ADMET: Excretion

Clearance (CL):	5.876
Half-life (T1/2):	0.614

ADMET: Toxicity

hERG Blockers:	0.373
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.458
Carcinogencity:	0.772
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC470481

Natural Product ID:	NPC470481
*Common Name:**	HXWIJPIEAIUMKA-KJDJIVLTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HXWIJPIEAIUMKA-KJDJIVLTSA-N
Standard InCHI:	InChI=1S/C22H28N2O4/c1-5-15-14-8-10-23(3)11-9-22(21(15)27)16-6-7-17(28-4)20(26)19(16)24(13(2)25)18(22)12-14/h5-7,14,18,26H,8-12H2,1-4H3/b15-5-/t14-,18-,22+/m0/s1
SMILES:	C/C=C1/[C@H]2CCN(CC[C@]3(C1=O)[C@H](C2)N(c1c3ccc(c1O)OC)C(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047334
PubChem CID:	70684076
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003756] Condylocarpan 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
NPO32721	geissospermum reticulatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22551062]

☑ 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
GI50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1021	Organism	Leishmania infantum	Leishmania infantum	GI50	>	100.0	ug.mL-1	PMID[486713]

☑ 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 NPC470481 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	372
0.1-0.2	1642
0.2-0.3	7168
0.3-0.4	10535
0.4-0.5	9696
0.5-0.6	11671
0.6-0.7	1482
0.7-0.8	125
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470482
0.8976	High Similarity	NPC470480
0.8341	Intermediate Similarity	NPC10732
0.8283	Intermediate Similarity	NPC161804
0.8	Intermediate Similarity	NPC163829
0.7925	Intermediate Similarity	NPC126556
0.7799	Intermediate Similarity	NPC207873
0.7799	Intermediate Similarity	NPC100573
0.7794	Intermediate Similarity	NPC100863
0.7788	Intermediate Similarity	NPC158551
0.7743	Intermediate Similarity	NPC477395
0.7736	Intermediate Similarity	NPC119722
0.7718	Intermediate Similarity	NPC127178
0.7707	Intermediate Similarity	NPC17677
0.7681	Intermediate Similarity	NPC471489
0.7664	Intermediate Similarity	NPC2905
0.7661	Intermediate Similarity	NPC148124
0.7642	Intermediate Similarity	NPC269449
0.7639	Intermediate Similarity	NPC182853
0.7621	Intermediate Similarity	NPC71124
0.7617	Intermediate Similarity	NPC114468
0.7615	Intermediate Similarity	NPC99724
0.7615	Intermediate Similarity	NPC7560
0.7615	Intermediate Similarity	NPC76478
0.7581	Intermediate Similarity	NPC148391
0.7571	Intermediate Similarity	NPC268077
0.757	Intermediate Similarity	NPC159815
0.7569	Intermediate Similarity	NPC318525
0.7569	Intermediate Similarity	NPC10653
0.7558	Intermediate Similarity	NPC134702
0.7557	Intermediate Similarity	NPC285254
0.7547	Intermediate Similarity	NPC90185
0.7536	Intermediate Similarity	NPC293624
0.7524	Intermediate Similarity	NPC207971
0.7523	Intermediate Similarity	NPC222046
0.7523	Intermediate Similarity	NPC248903
0.7522	Intermediate Similarity	NPC291173
0.7511	Intermediate Similarity	NPC19175
0.7477	Intermediate Similarity	NPC26928
0.7463	Intermediate Similarity	NPC196231
0.7455	Intermediate Similarity	NPC128476
0.7455	Intermediate Similarity	NPC118189
0.7452	Intermediate Similarity	NPC138615
0.7452	Intermediate Similarity	NPC265642
0.7452	Intermediate Similarity	NPC132874
0.7452	Intermediate Similarity	NPC218733
0.7444	Intermediate Similarity	NPC471513
0.7427	Intermediate Similarity	NPC254957
0.7427	Intermediate Similarity	NPC470485
0.7418	Intermediate Similarity	NPC212123
0.7416	Intermediate Similarity	NPC5374
0.7407	Intermediate Similarity	NPC127996
0.7406	Intermediate Similarity	NPC475147
0.7379	Intermediate Similarity	NPC473004
0.7376	Intermediate Similarity	NPC298339
0.7371	Intermediate Similarity	NPC477393
0.7371	Intermediate Similarity	NPC195787
0.7371	Intermediate Similarity	NPC246140
0.7364	Intermediate Similarity	NPC288110
0.7361	Intermediate Similarity	NPC295479
0.7361	Intermediate Similarity	NPC220241
0.7354	Intermediate Similarity	NPC122886
0.735	Intermediate Similarity	NPC287152
0.7339	Intermediate Similarity	NPC298449
0.7336	Intermediate Similarity	NPC308943
0.733	Intermediate Similarity	NPC470483
0.7324	Intermediate Similarity	NPC470484
0.7317	Intermediate Similarity	NPC477186
0.7311	Intermediate Similarity	NPC1464
0.7308	Intermediate Similarity	NPC477396
0.7306	Intermediate Similarity	NPC301163
0.7304	Intermediate Similarity	NPC262725
0.7301	Intermediate Similarity	NPC477397
0.7299	Intermediate Similarity	NPC67904
0.7297	Intermediate Similarity	NPC46259
0.7295	Intermediate Similarity	NPC204970
0.729	Intermediate Similarity	NPC477161
0.7289	Intermediate Similarity	NPC13249
0.7289	Intermediate Similarity	NPC473458
0.7286	Intermediate Similarity	NPC23080
0.7286	Intermediate Similarity	NPC193906
0.7281	Intermediate Similarity	NPC82541
0.7269	Intermediate Similarity	NPC477160
0.7269	Intermediate Similarity	NPC475133
0.726	Intermediate Similarity	NPC55470
0.7243	Intermediate Similarity	NPC14339
0.7228	Intermediate Similarity	NPC98416
0.7227	Intermediate Similarity	NPC471531
0.7205	Intermediate Similarity	NPC172222
0.72	Intermediate Similarity	NPC231924
0.7198	Intermediate Similarity	NPC174629
0.7195	Intermediate Similarity	NPC195636
0.7194	Intermediate Similarity	NPC135006
0.7188	Intermediate Similarity	NPC71539
0.7188	Intermediate Similarity	NPC250960
0.7183	Intermediate Similarity	NPC469732
0.7181	Intermediate Similarity	NPC74216
0.7173	Intermediate Similarity	NPC469539
0.7173	Intermediate Similarity	NPC469540
0.7172	Intermediate Similarity	NPC33507
0.7171	Intermediate Similarity	NPC473007
0.7169	Intermediate Similarity	NPC305542
0.7168	Intermediate Similarity	NPC266994
0.7163	Intermediate Similarity	NPC87714
0.7163	Intermediate Similarity	NPC473422
0.7162	Intermediate Similarity	NPC195120
0.7162	Intermediate Similarity	NPC87560
0.7156	Intermediate Similarity	NPC24228
0.7156	Intermediate Similarity	NPC474366
0.715	Intermediate Similarity	NPC162694
0.7143	Intermediate Similarity	NPC230313
0.7143	Intermediate Similarity	NPC85613
0.7143	Intermediate Similarity	NPC243626
0.7136	Intermediate Similarity	NPC30749
0.7136	Intermediate Similarity	NPC268223
0.7124	Intermediate Similarity	NPC477394
0.7116	Intermediate Similarity	NPC41216
0.7115	Intermediate Similarity	NPC473569
0.7115	Intermediate Similarity	NPC473008
0.7111	Intermediate Similarity	NPC251071
0.7108	Intermediate Similarity	NPC270301
0.71	Intermediate Similarity	NPC160113
0.71	Intermediate Similarity	NPC476220
0.7098	Intermediate Similarity	NPC476069
0.7093	Intermediate Similarity	NPC476436
0.7081	Intermediate Similarity	NPC22476
0.7081	Intermediate Similarity	NPC203628
0.7071	Intermediate Similarity	NPC299582
0.7069	Intermediate Similarity	NPC154922
0.7065	Intermediate Similarity	NPC73280
0.7059	Intermediate Similarity	NPC5167
0.7059	Intermediate Similarity	NPC39822
0.7056	Intermediate Similarity	NPC138830
0.7054	Intermediate Similarity	NPC475609
0.704	Intermediate Similarity	NPC313327
0.7037	Intermediate Similarity	NPC473460
0.7028	Intermediate Similarity	NPC170333
0.7022	Intermediate Similarity	NPC157983
0.7022	Intermediate Similarity	NPC118154
0.7019	Intermediate Similarity	NPC21425
0.7018	Intermediate Similarity	NPC16249
0.7018	Intermediate Similarity	NPC222561
0.7015	Intermediate Similarity	NPC471604
0.7014	Intermediate Similarity	NPC78284
0.7014	Intermediate Similarity	NPC116178
0.7009	Intermediate Similarity	NPC77777
0.699	Remote Similarity	NPC314659
0.699	Remote Similarity	NPC149285
0.6982	Remote Similarity	NPC217903
0.698	Remote Similarity	NPC96901
0.6979	Remote Similarity	NPC476258
0.6979	Remote Similarity	NPC304837
0.6979	Remote Similarity	NPC41501
0.6976	Remote Similarity	NPC166169
0.6968	Remote Similarity	NPC471532
0.6963	Remote Similarity	NPC112937
0.6957	Remote Similarity	NPC302235
0.6952	Remote Similarity	NPC474059
0.6948	Remote Similarity	NPC303214
0.6944	Remote Similarity	NPC254045
0.6944	Remote Similarity	NPC64576
0.6944	Remote Similarity	NPC232600
0.6944	Remote Similarity	NPC201055
0.6944	Remote Similarity	NPC151470
0.6942	Remote Similarity	NPC197335
0.6941	Remote Similarity	NPC478075
0.694	Remote Similarity	NPC476429
0.6934	Remote Similarity	NPC94499
0.6926	Remote Similarity	NPC470821
0.692	Remote Similarity	NPC234772
0.692	Remote Similarity	NPC113455
0.6916	Remote Similarity	NPC279665
0.6912	Remote Similarity	NPC97086
0.6906	Remote Similarity	NPC321166
0.69	Remote Similarity	NPC153631
0.6893	Remote Similarity	NPC222524
0.6892	Remote Similarity	NPC218303
0.689	Remote Similarity	NPC276674
0.689	Remote Similarity	NPC33902
0.689	Remote Similarity	NPC87391
0.6887	Remote Similarity	NPC206109
0.6887	Remote Similarity	NPC114039
0.6887	Remote Similarity	NPC63152
0.6878	Remote Similarity	NPC471561
0.6875	Remote Similarity	NPC176113
0.6875	Remote Similarity	NPC189661
0.6869	Remote Similarity	NPC147091
0.6864	Remote Similarity	NPC198160
0.6852	Remote Similarity	NPC207239
0.6852	Remote Similarity	NPC267414
0.685	Remote Similarity	NPC226428
0.6849	Remote Similarity	NPC133156
0.6842	Remote Similarity	NPC102760
0.684	Remote Similarity	NPC1820
0.6837	Remote Similarity	NPC119669
0.6835	Remote Similarity	NPC473005
0.6835	Remote Similarity	NPC243483
0.6835	Remote Similarity	NPC232533
0.6833	Remote Similarity	NPC205926
0.6833	Remote Similarity	NPC120239

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 NPC470481 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	639
0.2-0.3	958
0.3-0.4	1891
0.4-0.5	2970
0.5-0.6	2039
0.6-0.7	416
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7523	Intermediate Similarity	NPD2899	Discontinued
0.7393	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5071	Phase 2
0.7206	Intermediate Similarity	NPD7281	Phase 3
0.7206	Intermediate Similarity	NPD7280	Phase 3
0.7188	Intermediate Similarity	NPD824	Approved
0.7163	Intermediate Similarity	NPD4465	Phase 2
0.7163	Intermediate Similarity	NPD4467	Phase 2
0.7111	Intermediate Similarity	NPD6997	Phase 2
0.7083	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5025	Approved
0.7067	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4859	Phase 1
0.705	Intermediate Similarity	NPD5183	Approved
0.705	Intermediate Similarity	NPD5186	Approved
0.7045	Intermediate Similarity	NPD683	Approved
0.7023	Intermediate Similarity	NPD6321	Discontinued
0.7022	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7278	Phase 2
0.7004	Intermediate Similarity	NPD7279	Phase 2
0.7	Intermediate Similarity	NPD2488	Approved
0.7	Intermediate Similarity	NPD2490	Approved
0.6995	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4493	Discontinued
0.6966	Remote Similarity	NPD7048	Phase 3
0.6951	Remote Similarity	NPD7559	Phase 2
0.6944	Remote Similarity	NPD3452	Approved
0.6944	Remote Similarity	NPD3450	Approved
0.6944	Remote Similarity	NPD2493	Approved
0.6944	Remote Similarity	NPD2494	Approved
0.6938	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4582	Approved
0.6927	Remote Similarity	NPD4583	Approved
0.6923	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3893	Discontinued
0.691	Remote Similarity	NPD6625	Approved
0.6906	Remote Similarity	NPD4455	Discontinued
0.6894	Remote Similarity	NPD4846	Phase 2
0.6881	Remote Similarity	NPD4002	Approved
0.6881	Remote Similarity	NPD4004	Approved
0.6878	Remote Similarity	NPD1221	Approved
0.6872	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7263	Phase 2
0.6861	Remote Similarity	NPD3888	Discontinued
0.685	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4040	Phase 1
0.6849	Remote Similarity	NPD3298	Approved
0.6845	Remote Similarity	NPD7479	Phase 2
0.6844	Remote Similarity	NPD8149	Discontinued
0.6835	Remote Similarity	NPD2491	Approved
0.6835	Remote Similarity	NPD3448	Approved
0.6832	Remote Similarity	NPD6457	Approved
0.6828	Remote Similarity	NPD5496	Approved
0.6821	Remote Similarity	NPD1670	Discontinued
0.6816	Remote Similarity	NPD1945	Phase 1
0.6814	Remote Similarity	NPD1220	Phase 1
0.6814	Remote Similarity	NPD2898	Approved
0.6812	Remote Similarity	NPD6297	Approved
0.6812	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3437	Discontinued
0.6796	Remote Similarity	NPD5312	Approved
0.6796	Remote Similarity	NPD3793	Phase 3
0.6796	Remote Similarity	NPD5313	Approved
0.6791	Remote Similarity	NPD5582	Discontinued
0.6789	Remote Similarity	NPD6238	Discontinued
0.6787	Remote Similarity	NPD4596	Phase 1
0.6786	Remote Similarity	NPD4494	Approved
0.6786	Remote Similarity	NPD4492	Approved
0.6781	Remote Similarity	NPD4981	Phase 2
0.6778	Remote Similarity	NPD6517	Phase 3
0.6778	Remote Similarity	NPD6716	Phase 1
0.6771	Remote Similarity	NPD5860	Discontinued
0.677	Remote Similarity	NPD7047	Phase 3
0.6761	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5564	Approved
0.6759	Remote Similarity	NPD2975	Approved
0.6759	Remote Similarity	NPD2974	Approved
0.6759	Remote Similarity	NPD2973	Approved
0.6758	Remote Similarity	NPD3057	Approved
0.6757	Remote Similarity	NPD4082	Approved
0.675	Remote Similarity	NPD5977	Approved
0.675	Remote Similarity	NPD5978	Approved
0.6749	Remote Similarity	NPD2821	Approved
0.6743	Remote Similarity	NPD4580	Approved
0.6742	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5676	Approved
0.674	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3639	Approved
0.6735	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3640	Phase 3
0.6735	Remote Similarity	NPD3641	Approved
0.6717	Remote Similarity	NPD6875	Approved
0.6717	Remote Similarity	NPD6876	Approved
0.6716	Remote Similarity	NPD1293	Approved
0.6713	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3912	Discontinued
0.671	Remote Similarity	NPD7820	Phase 3
0.6697	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7907	Approved
0.6695	Remote Similarity	NPD7922	Phase 1
0.6683	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4083	Discontinued
0.6683	Remote Similarity	NPD7110	Phase 1
0.6682	Remote Similarity	NPD6853	Approved
0.6682	Remote Similarity	NPD6851	Approved
0.6682	Remote Similarity	NPD2972	Approved
0.6682	Remote Similarity	NPD3533	Approved
0.6682	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4665	Approved
0.6681	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD7291	Discontinued
0.6667	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7186	Phase 3
0.6651	Remote Similarity	NPD4668	Phase 2
0.6637	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7225	Discontinued
0.6636	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2971	Approved
0.6635	Remote Similarity	NPD2968	Approved
0.6634	Remote Similarity	NPD4166	Phase 2
0.6624	Remote Similarity	NPD6723	Discontinued
0.6624	Remote Similarity	NPD4373	Phase 2
0.6623	Remote Similarity	NPD7805	Phase 3
0.6621	Remote Similarity	NPD3297	Approved
0.662	Remote Similarity	NPD4515	Suspended
0.662	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5823	Approved
0.6617	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3472	Approved
0.6607	Remote Similarity	NPD4022	Approved
0.6607	Remote Similarity	NPD2906	Approved
0.6607	Remote Similarity	NPD2907	Approved
0.6605	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6618	Phase 2
0.6591	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.658	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3416	Discontinued
0.655	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3372	Discontinued
0.6545	Remote Similarity	NPD743	Approved
0.6545	Remote Similarity	NPD5608	Approved
0.6545	Remote Similarity	NPD5609	Approved
0.6544	Remote Similarity	NPD4539	Phase 1
0.6538	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6873	Phase 2
0.6516	Remote Similarity	NPD4107	Approved
0.6498	Remote Similarity	NPD6199	Discontinued
0.6498	Remote Similarity	NPD5937	Approved
0.6498	Remote Similarity	NPD4952	Phase 3
0.6496	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6339	Approved
0.6495	Remote Similarity	NPD6340	Approved
0.6491	Remote Similarity	NPD5866	Approved
0.649	Remote Similarity	NPD27	Approved
0.649	Remote Similarity	NPD2489	Approved
0.649	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7043	Discontinued
0.6483	Remote Similarity	NPD3259	Approved
0.6481	Remote Similarity	NPD7628	Phase 3
0.6481	Remote Similarity	NPD7630	Phase 3
0.6481	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5914	Approved
0.6473	Remote Similarity	NPD6644	Discontinued
0.6471	Remote Similarity	NPD6962	Phase 2
0.6471	Remote Similarity	NPD6874	Approved
0.6468	Remote Similarity	NPD5610	Approved
0.6468	Remote Similarity	NPD4466	Phase 1
0.6461	Remote Similarity	NPD6790	Phase 1
0.646	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7302	Phase 3
0.646	Remote Similarity	NPD7300	Phase 3
0.6456	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD8091	Phase 3
0.6453	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4885	Approved
0.6442	Remote Similarity	NPD5242	Approved
0.6442	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7906	Approved
0.6429	Remote Similarity	NPD6478	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