NPASS Compound

Structure

NPC185742 OpenBabel07101718182D 26 30 0 0 1 0 0 0 0 0999 V2000 -0.2632 -1.1357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3652 2.1144 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 -1.9465 -0.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3044 -0.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3096 -0.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4901 -0.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4384 0.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 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 -2.6831 -0.3090 0.0000 C 0 0 1 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 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 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 -1.1212 0.9092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 2 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 -1.2520 -1.2847 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1513 0.6657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6285 -2.0665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3953 1.8709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1314 0.3640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 15 2 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 9 22 1 0 0 0 0 10 26 1 0 0 0 0 11 20 1 0 0 0 0 11 26 1 0 0 0 0 12 8 1 1 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 1 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 17 16 1 1 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 19 1 6 0 0 0 22 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.17
Volume:	355.666
LogP:	0.164
LogD:	1.13
LogS:	-1.159
# Rotatable Bonds:	2
TPSA:	74.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	5.675
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.576
MDCK Permeability:	1.105119736166671e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.92
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.518
Plasma Protein Binding (PPB):	16.839519500732422%
Volume Distribution (VD):	1.813
Pgp-substrate:	77.39994049072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.39
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	8.339
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.055
Carcinogencity:	0.702
Eye Corrosion:	0.004
Eye Irritation:	0.102
Respiratory Toxicity:	0.6

Download Data

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

Natural Product: NPC185742

Natural Product ID:	NPC185742
*Common Name:**	Alpneumine H
IUPAC Name:	n.a.
Synonyms:	Alpneumine H
Standard InCHIKey:	OSMMAUUKWDERDD-ZRWJFXDNSA-N
Standard InCHI:	InChI=1S/C20H24N2O4/c1-22(24)9-7-14-12-8-10-26-11-20(14,19(23)25-2)18-16(17(12)22)13-5-3-4-6-15(13)21-18/h3-6,12,14,17,21H,7-11H2,1-2H3/t12-,14-,17+,20-,22-/m0/s1
SMILES:	COC(=O)[C@@]12COCC[C@H]3[C@@H]1CCN(=O)([C@H]3c1c2[nH]c2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1165844
PubChem CID:	46906334
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO25579	Alstonia pneumatophora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20576577]
NPO25579	Alstonia pneumatophora	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	100000.0	nM	PMID[466530]

☑ 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 NPC185742 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	330
0.1-0.2	1661
0.2-0.3	8606
0.3-0.4	22530
0.4-0.5	4955
0.5-0.6	2403
0.6-0.7	1826
0.7-0.8	336
0.8-0.85	36
0.85-0.9	10
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475847
0.9149	High Similarity	NPC162730
0.9048	High Similarity	NPC474116
0.8978	High Similarity	NPC474121
0.8466	Intermediate Similarity	NPC329858
0.8368	Intermediate Similarity	NPC314333
0.8358	Intermediate Similarity	NPC475778
0.8281	Intermediate Similarity	NPC55493
0.8182	Intermediate Similarity	NPC137589
0.8168	Intermediate Similarity	NPC234999
0.803	Intermediate Similarity	NPC241024
0.803	Intermediate Similarity	NPC469743
0.798	Intermediate Similarity	NPC52557
0.79	Intermediate Similarity	NPC214428
0.7882	Intermediate Similarity	NPC277350
0.785	Intermediate Similarity	NPC469720
0.7846	Intermediate Similarity	NPC175474
0.7723	Intermediate Similarity	NPC79129
0.7723	Intermediate Similarity	NPC81654
0.7723	Intermediate Similarity	NPC249150
0.7723	Intermediate Similarity	NPC49196
0.7723	Intermediate Similarity	NPC195461
0.7723	Intermediate Similarity	NPC313985
0.7714	Intermediate Similarity	NPC469928
0.7642	Intermediate Similarity	NPC96321
0.763	Intermediate Similarity	NPC330009
0.7624	Intermediate Similarity	NPC50503
0.7585	Intermediate Similarity	NPC477065
0.7576	Intermediate Similarity	NPC111602
0.7576	Intermediate Similarity	NPC102338
0.7576	Intermediate Similarity	NPC196251
0.7576	Intermediate Similarity	NPC63199
0.7559	Intermediate Similarity	NPC473041
0.7512	Intermediate Similarity	NPC472210
0.7512	Intermediate Similarity	NPC269886
0.7512	Intermediate Similarity	NPC247735
0.7512	Intermediate Similarity	NPC472295
0.7512	Intermediate Similarity	NPC81802
0.75	Intermediate Similarity	NPC19679
0.7489	Intermediate Similarity	NPC311906
0.7488	Intermediate Similarity	NPC469736
0.7487	Intermediate Similarity	NPC469896
0.7463	Intermediate Similarity	NPC472113
0.7462	Intermediate Similarity	NPC472119
0.745	Intermediate Similarity	NPC472112
0.7389	Intermediate Similarity	NPC220151
0.7389	Intermediate Similarity	NPC19692
0.7387	Intermediate Similarity	NPC475720
0.7387	Intermediate Similarity	NPC474192
0.7368	Intermediate Similarity	NPC469541
0.7353	Intermediate Similarity	NPC245916
0.7295	Intermediate Similarity	NPC294909
0.7295	Intermediate Similarity	NPC254240
0.7295	Intermediate Similarity	NPC128265
0.7295	Intermediate Similarity	NPC312870
0.7295	Intermediate Similarity	NPC199851
0.729	Intermediate Similarity	NPC472291
0.7282	Intermediate Similarity	NPC329688
0.7282	Intermediate Similarity	NPC189812
0.7277	Intermediate Similarity	NPC473105
0.7269	Intermediate Similarity	NPC475816
0.7259	Intermediate Similarity	NPC219336
0.725	Intermediate Similarity	NPC472209
0.725	Intermediate Similarity	NPC472107
0.725	Intermediate Similarity	NPC79062
0.7234	Intermediate Similarity	NPC473297
0.723	Intermediate Similarity	NPC471304
0.7208	Intermediate Similarity	NPC217372
0.7208	Intermediate Similarity	NPC15573
0.7208	Intermediate Similarity	NPC183662
0.7206	Intermediate Similarity	NPC472292
0.7184	Intermediate Similarity	NPC472293
0.7178	Intermediate Similarity	NPC472323
0.7163	Intermediate Similarity	NPC472296
0.7163	Intermediate Similarity	NPC472297
0.7143	Intermediate Similarity	NPC148183
0.7143	Intermediate Similarity	NPC152768
0.7136	Intermediate Similarity	NPC2395
0.7136	Intermediate Similarity	NPC181502
0.7136	Intermediate Similarity	NPC85066
0.7135	Intermediate Similarity	NPC282339
0.7135	Intermediate Similarity	NPC99632
0.713	Intermediate Similarity	NPC475602
0.713	Intermediate Similarity	NPC473540
0.7121	Intermediate Similarity	NPC234987
0.7119	Intermediate Similarity	NPC478080
0.7108	Intermediate Similarity	NPC95783
0.7107	Intermediate Similarity	NPC13367
0.7103	Intermediate Similarity	NPC271862
0.7101	Intermediate Similarity	NPC11445
0.7087	Intermediate Similarity	NPC45850
0.7085	Intermediate Similarity	NPC213468
0.7082	Intermediate Similarity	NPC17437
0.7077	Intermediate Similarity	NPC317430
0.7065	Intermediate Similarity	NPC139291
0.7065	Intermediate Similarity	NPC143533
0.7065	Intermediate Similarity	NPC472108
0.7056	Intermediate Similarity	NPC258062
0.7056	Intermediate Similarity	NPC127677
0.7053	Intermediate Similarity	NPC157828
0.7053	Intermediate Similarity	NPC195239
0.705	Intermediate Similarity	NPC15840
0.7044	Intermediate Similarity	NPC66210
0.7044	Intermediate Similarity	NPC160381
0.704	Intermediate Similarity	NPC235885
0.7035	Intermediate Similarity	NPC84827
0.7035	Intermediate Similarity	NPC14113
0.7035	Intermediate Similarity	NPC476326
0.7035	Intermediate Similarity	NPC145885
0.7035	Intermediate Similarity	NPC111275
0.703	Intermediate Similarity	NPC258480
0.7028	Intermediate Similarity	NPC98715
0.702	Intermediate Similarity	NPC329338
0.702	Intermediate Similarity	NPC469726
0.7018	Intermediate Similarity	NPC474412
0.701	Intermediate Similarity	NPC271797
0.701	Intermediate Similarity	NPC21174
0.7009	Intermediate Similarity	NPC46225
0.7009	Intermediate Similarity	NPC225821
0.7005	Intermediate Similarity	NPC151976
0.7005	Intermediate Similarity	NPC87856
0.6996	Remote Similarity	NPC81939
0.6995	Remote Similarity	NPC143457
0.699	Remote Similarity	NPC472097
0.6986	Remote Similarity	NPC232130
0.6986	Remote Similarity	NPC132211
0.6981	Remote Similarity	NPC476874
0.6981	Remote Similarity	NPC260900
0.6978	Remote Similarity	NPC478078
0.6976	Remote Similarity	NPC183805
0.6974	Remote Similarity	NPC70155
0.6972	Remote Similarity	NPC267965
0.697	Remote Similarity	NPC472123
0.6968	Remote Similarity	NPC52254
0.6966	Remote Similarity	NPC475666
0.6963	Remote Similarity	NPC18661
0.6961	Remote Similarity	NPC235684
0.6952	Remote Similarity	NPC67288
0.694	Remote Similarity	NPC477066
0.6934	Remote Similarity	NPC300183
0.6931	Remote Similarity	NPC113626
0.6931	Remote Similarity	NPC71037
0.6923	Remote Similarity	NPC281049
0.6923	Remote Similarity	NPC82070
0.6916	Remote Similarity	NPC314648
0.6912	Remote Similarity	NPC469460
0.6912	Remote Similarity	NPC126066
0.6912	Remote Similarity	NPC52262
0.691	Remote Similarity	NPC477067
0.691	Remote Similarity	NPC478082
0.691	Remote Similarity	NPC478081
0.6909	Remote Similarity	NPC203614
0.6909	Remote Similarity	NPC476114
0.6909	Remote Similarity	NPC204491
0.6907	Remote Similarity	NPC225319
0.6904	Remote Similarity	NPC154293
0.6901	Remote Similarity	NPC193761
0.6901	Remote Similarity	NPC476073
0.69	Remote Similarity	NPC267885
0.6897	Remote Similarity	NPC472104
0.6895	Remote Similarity	NPC33421
0.6895	Remote Similarity	NPC229348
0.689	Remote Similarity	NPC289299
0.689	Remote Similarity	NPC57994
0.6889	Remote Similarity	NPC21638
0.6878	Remote Similarity	NPC282092
0.6878	Remote Similarity	NPC315555
0.6878	Remote Similarity	NPC62749
0.6872	Remote Similarity	NPC176983
0.6872	Remote Similarity	NPC16667
0.6872	Remote Similarity	NPC33949
0.6869	Remote Similarity	NPC280548
0.6866	Remote Similarity	NPC260075
0.6864	Remote Similarity	NPC478157
0.6863	Remote Similarity	NPC472294
0.6862	Remote Similarity	NPC329982
0.6861	Remote Similarity	NPC472099
0.686	Remote Similarity	NPC469501
0.686	Remote Similarity	NPC469470
0.6858	Remote Similarity	NPC472762
0.6857	Remote Similarity	NPC472116
0.6852	Remote Similarity	NPC315545
0.6852	Remote Similarity	NPC314297
0.685	Remote Similarity	NPC149155
0.685	Remote Similarity	NPC203468
0.685	Remote Similarity	NPC110500
0.6847	Remote Similarity	NPC476428
0.6844	Remote Similarity	NPC266192
0.6844	Remote Similarity	NPC475271
0.6842	Remote Similarity	NPC88315
0.684	Remote Similarity	NPC74413
0.6839	Remote Similarity	NPC29285
0.6839	Remote Similarity	NPC285469
0.6832	Remote Similarity	NPC248041
0.6832	Remote Similarity	NPC283219
0.6832	Remote Similarity	NPC126709
0.6821	Remote Similarity	NPC248117
0.6818	Remote Similarity	NPC478074
0.6818	Remote Similarity	NPC221100
0.6818	Remote Similarity	NPC78020

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 NPC185742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	518
0.2-0.3	726
0.3-0.4	1850
0.4-0.5	2860
0.5-0.6	2307
0.6-0.7	639
0.7-0.8	58
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8368	Intermediate Similarity	NPD4499	Approved
0.7723	Intermediate Similarity	NPD4601	Approved
0.7723	Intermediate Similarity	NPD4600	Approved
0.7415	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD4500	Approved
0.7295	Intermediate Similarity	NPD4501	Approved
0.7281	Intermediate Similarity	NPD6770	Approved
0.7264	Intermediate Similarity	NPD4506	Discontinued
0.7233	Intermediate Similarity	NPD5003	Discontinued
0.7165	Intermediate Similarity	NPD2844	Phase 3
0.7115	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6176	Phase 1
0.7082	Intermediate Similarity	NPD8358	Approved
0.7075	Intermediate Similarity	NPD5426	Phase 3
0.7024	Intermediate Similarity	NPD2565	Phase 2
0.7024	Intermediate Similarity	NPD2564	Approved
0.698	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2092	Phase 2
0.698	Remote Similarity	NPD2095	Phase 2
0.698	Remote Similarity	NPD2094	Phase 2
0.6977	Remote Similarity	NPD2509	Approved
0.6977	Remote Similarity	NPD2510	Approved
0.6963	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2920	Discontinued
0.6946	Remote Similarity	NPD2091	Phase 2
0.6946	Remote Similarity	NPD2096	Phase 2
0.6916	Remote Similarity	NPD5901	Discontinued
0.6909	Remote Similarity	NPD3389	Approved
0.6909	Remote Similarity	NPD3393	Approved
0.6909	Remote Similarity	NPD3394	Approved
0.689	Remote Similarity	NPD4602	Approved
0.6888	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7864	Approved
0.6853	Remote Similarity	NPD7863	Approved
0.685	Remote Similarity	NPD482	Approved
0.6849	Remote Similarity	NPD7454	Approved
0.6849	Remote Similarity	NPD7455	Approved
0.684	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8098	Approved
0.6828	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6664	Approved
0.682	Remote Similarity	NPD8423	Phase 2
0.682	Remote Similarity	NPD8399	Phase 1
0.6818	Remote Similarity	NPD7866	Approved
0.6816	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1534	Approved
0.6812	Remote Similarity	NPD7233	Approved
0.6812	Remote Similarity	NPD7234	Approved
0.6806	Remote Similarity	NPD7010	Phase 3
0.6804	Remote Similarity	NPD7470	Discontinued
0.68	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5473	Discontinued
0.6792	Remote Similarity	NPD4397	Phase 1
0.6759	Remote Similarity	NPD8283	Approved
0.6759	Remote Similarity	NPD8282	Approved
0.6759	Remote Similarity	NPD56	Approved
0.6743	Remote Similarity	NPD2916	Discontinued
0.6731	Remote Similarity	NPD4334	Discontinued
0.673	Remote Similarity	NPD4427	Phase 2
0.6716	Remote Similarity	NPD750	Phase 2
0.6714	Remote Similarity	NPD7777	Approved
0.6714	Remote Similarity	NPD53	Approved
0.6714	Remote Similarity	NPD7778	Approved
0.6712	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1325	Approved
0.67	Remote Similarity	NPD1326	Approved
0.6698	Remote Similarity	NPD6226	Phase 3
0.6698	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7878	Phase 2
0.6683	Remote Similarity	NPD4948	Discontinued
0.6682	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3947	Discontinued
0.6682	Remote Similarity	NPD6987	Phase 1
0.6667	Remote Similarity	NPD5913	Phase 3
0.6667	Remote Similarity	NPD7688	Phase 1
0.6667	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5475	Discontinued
0.6652	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6479	Discontinued
0.665	Remote Similarity	NPD5596	Phase 2
0.664	Remote Similarity	NPD8467	Approved
0.664	Remote Similarity	NPD8466	Approved
0.664	Remote Similarity	NPD8465	Approved
0.6637	Remote Similarity	NPD5293	Phase 2
0.6636	Remote Similarity	NPD7946	Pre-registration
0.6636	Remote Similarity	NPD6529	Discontinued
0.6636	Remote Similarity	NPD8072	Approved
0.6623	Remote Similarity	NPD7824	Approved
0.6622	Remote Similarity	NPD8097	Phase 3
0.6622	Remote Similarity	NPD8096	Phase 3
0.6621	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7865	Approved
0.6618	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2144	Approved
0.6617	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7955	Approved
0.6612	Remote Similarity	NPD7956	Approved
0.6605	Remote Similarity	NPD6999	Discontinued
0.6605	Remote Similarity	NPD6248	Phase 2
0.6605	Remote Similarity	NPD6249	Phase 2
0.6605	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD3038	Discontinued
0.6588	Remote Similarity	NPD2336	Approved
0.6588	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7708	Approved
0.6585	Remote Similarity	NPD4076	Approved
0.6585	Remote Similarity	NPD4079	Approved
0.6579	Remote Similarity	NPD6995	Phase 1
0.6579	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7957	Phase 1
0.6575	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3319	Phase 1
0.657	Remote Similarity	NPD3320	Approved
0.657	Remote Similarity	NPD3318	Approved
0.6569	Remote Similarity	NPD4075	Phase 2
0.6569	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4315	Phase 2
0.6552	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4852	Phase 2
0.6546	Remote Similarity	NPD7803	Approved
0.6538	Remote Similarity	NPD7950	Approved
0.6538	Remote Similarity	NPD7951	Approved
0.6538	Remote Similarity	NPD7791	Approved
0.6538	Remote Similarity	NPD7952	Approved
0.6538	Remote Similarity	NPD7953	Approved
0.6538	Remote Similarity	NPD7790	Approved
0.6538	Remote Similarity	NPD7789	Approved
0.6537	Remote Similarity	NPD8459	Approved
0.6537	Remote Similarity	NPD8426	Approved
0.6537	Remote Similarity	NPD3505	Approved
0.6537	Remote Similarity	NPD8425	Approved
0.6537	Remote Similarity	NPD7730	Approved
0.6537	Remote Similarity	NPD7731	Approved
0.6537	Remote Similarity	NPD8460	Approved
0.6537	Remote Similarity	NPD3506	Approved
0.6537	Remote Similarity	NPD7869	Discontinued
0.6534	Remote Similarity	NPD8364	Approved
0.6534	Remote Similarity	NPD8363	Approved
0.6533	Remote Similarity	NPD8160	Phase 2
0.6524	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7271	Approved
0.652	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3794	Approved
0.6518	Remote Similarity	NPD3795	Approved
0.6516	Remote Similarity	NPD6376	Discontinued
0.6515	Remote Similarity	NPD2214	Approved
0.6515	Remote Similarity	NPD2213	Approved
0.6513	Remote Similarity	NPD7882	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8428	Approved
0.651	Remote Similarity	NPD8429	Approved
0.651	Remote Similarity	NPD8427	Approved
0.6507	Remote Similarity	NPD6227	Discontinued
0.6507	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7001	Phase 3
0.65	Remote Similarity	NPD6635	Approved
0.6498	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5427	Suspended
0.6495	Remote Similarity	NPD7618	Phase 3
0.6495	Remote Similarity	NPD7619	Phase 3
0.6486	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7941	Phase 3
0.6486	Remote Similarity	NPD4520	Approved
0.6485	Remote Similarity	NPD7770	Phase 3
0.6484	Remote Similarity	NPD5487	Phase 1
0.6483	Remote Similarity	NPD5891	Approved
0.6482	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5444	Phase 1
0.6473	Remote Similarity	NPD5899	Approved
0.6473	Remote Similarity	NPD5897	Approved
0.6473	Remote Similarity	NPD5898	Approved
0.6468	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6978	Phase 2
0.6466	Remote Similarity	NPD6164	Phase 2
0.6466	Remote Similarity	NPD6165	Phase 2
0.6465	Remote Similarity	NPD2307	Discontinued
0.6462	Remote Similarity	NPD6281	Approved
0.6457	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8115	Approved
0.6455	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8114	Approved
0.6452	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8094	Discontinued
0.6441	Remote Similarity	NPD7666	Phase 3
0.6441	Remote Similarity	NPD7665	Phase 2
0.6439	Remote Similarity	NPD5065	Approved
0.6438	Remote Similarity	NPD8073	Approved
0.6435	Remote Similarity	NPD6206	Phase 1
0.6432	Remote Similarity	NPD5483	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