NPASS Compound

Structure

NPC469560 OpenBabel07101719512D 23 27 0 0 1 0 0 0 0 0999 V2000 1.3494 0.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5132 0.6191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0741 0.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1230 0.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4775 -0.0502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2820 -0.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.4271 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 0.0000 -1.6180 0.0000 C 0 0 0 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 -0.0976 -0.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4901 -1.0283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 -2.7058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.15
Volume:	318.153
LogP:	2.902
LogD:	2.736
LogS:	-4.849
# Rotatable Bonds:	1
TPSA:	40.62
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	4.538
Fsp3:	0.474
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:	-4.829
MDCK Permeability:	2.333309566893149e-05
Pgp-inhibitor:	0.883
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.885
Plasma Protein Binding (PPB):	65.23876190185547%
Volume Distribution (VD):	0.696
Pgp-substrate:	21.36186408996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.571
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.741
CYP2D6-inhibitor:	0.335
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	5.241
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.864
Skin Sensitization:	0.76
Carcinogencity:	0.929
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.67

Download Data

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

Natural Product: NPC469560

Natural Product ID:	NPC469560
*Common Name:**	Melodinine E
IUPAC Name:	n.a.
Synonyms:	Melodinine E
Standard InCHIKey:	LUXCFVAZXZITNG-MRTLOADZSA-N
Standard InCHI:	InChI=1S/C19H20N2O2/c1-2-18-9-5-11-20-17(23)12-14-13-6-3-4-7-15(13)21(19(14,18)20)16(22)8-10-18/h3-4,6-7,12H,2,5,8-11H2,1H3/t18-,19?/m1/s1
SMILES:	CC[C@@]12CCCN3C42N(C(=O)CC1)c1c(C4=CC3=O)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087385
PubChem CID:	44626860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002758] Rhazinilam 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
NPO33278	melodinus henryi	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20041704]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[544157]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[544157]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[544157]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[544157]

☑ 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 NPC469560 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	314
0.1-0.2	2178
0.2-0.3	11486
0.3-0.4	20161
0.4-0.5	6237
0.5-0.6	1941
0.6-0.7	333
0.7-0.8	36
0.8-0.85	8
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9248	High Similarity	NPC471123
0.8741	High Similarity	NPC473329
0.8299	Intermediate Similarity	NPC66936
0.8212	Intermediate Similarity	NPC471122
0.8117	Intermediate Similarity	NPC471124
0.8026	Intermediate Similarity	NPC222029
0.7974	Intermediate Similarity	NPC276085
0.78	Intermediate Similarity	NPC109787
0.775	Intermediate Similarity	NPC242269
0.7677	Intermediate Similarity	NPC113946
0.7655	Intermediate Similarity	NPC267508
0.7647	Intermediate Similarity	NPC117032
0.7619	Intermediate Similarity	NPC130251
0.7619	Intermediate Similarity	NPC315051
0.7568	Intermediate Similarity	NPC471164
0.7568	Intermediate Similarity	NPC470301
0.7423	Intermediate Similarity	NPC285622
0.7378	Intermediate Similarity	NPC470548
0.7372	Intermediate Similarity	NPC478076
0.7362	Intermediate Similarity	NPC355
0.7346	Intermediate Similarity	NPC475248
0.7346	Intermediate Similarity	NPC63047
0.7333	Intermediate Similarity	NPC22082
0.7333	Intermediate Similarity	NPC186284
0.7333	Intermediate Similarity	NPC301760
0.7312	Intermediate Similarity	NPC472120
0.7312	Intermediate Similarity	NPC472101
0.7284	Intermediate Similarity	NPC279527
0.7284	Intermediate Similarity	NPC214960
0.7266	Intermediate Similarity	NPC226143
0.7237	Intermediate Similarity	NPC469537
0.7233	Intermediate Similarity	NPC61013
0.7222	Intermediate Similarity	NPC472106
0.7205	Intermediate Similarity	NPC194881
0.7188	Intermediate Similarity	NPC36495
0.7188	Intermediate Similarity	NPC193410
0.717	Intermediate Similarity	NPC29285
0.7168	Intermediate Similarity	NPC128582
0.7162	Intermediate Similarity	NPC316104
0.7162	Intermediate Similarity	NPC162417
0.7153	Intermediate Similarity	NPC252794
0.7143	Intermediate Similarity	NPC248117
0.7143	Intermediate Similarity	NPC177684
0.7143	Intermediate Similarity	NPC291962
0.7143	Intermediate Similarity	NPC68650
0.7143	Intermediate Similarity	NPC225319
0.7134	Intermediate Similarity	NPC154602
0.7134	Intermediate Similarity	NPC243756
0.7125	Intermediate Similarity	NPC104345
0.7108	Intermediate Similarity	NPC139085
0.7108	Intermediate Similarity	NPC214626
0.7108	Intermediate Similarity	NPC251212
0.7099	Intermediate Similarity	NPC472117
0.7092	Intermediate Similarity	NPC161956
0.7092	Intermediate Similarity	NPC258531
0.7092	Intermediate Similarity	NPC112373
0.7042	Intermediate Similarity	NPC257490
0.7037	Intermediate Similarity	NPC309531
0.7037	Intermediate Similarity	NPC472102
0.7019	Intermediate Similarity	NPC123241
0.7007	Intermediate Similarity	NPC187231
0.7006	Intermediate Similarity	NPC161861
0.7	Intermediate Similarity	NPC286994
0.6994	Remote Similarity	NPC17273
0.6994	Remote Similarity	NPC469741
0.6994	Remote Similarity	NPC141612
0.6994	Remote Similarity	NPC135601
0.6993	Remote Similarity	NPC471574
0.6986	Remote Similarity	NPC145754
0.6971	Remote Similarity	NPC473569
0.695	Remote Similarity	NPC264580
0.6936	Remote Similarity	NPC259626
0.6933	Remote Similarity	NPC474058
0.6933	Remote Similarity	NPC315368
0.6928	Remote Similarity	NPC167724
0.6928	Remote Similarity	NPC224970
0.6928	Remote Similarity	NPC223595
0.6913	Remote Similarity	NPC207428
0.6905	Remote Similarity	NPC96901
0.6897	Remote Similarity	NPC473615
0.6894	Remote Similarity	NPC161827
0.689	Remote Similarity	NPC176983
0.689	Remote Similarity	NPC99632
0.689	Remote Similarity	NPC282339
0.689	Remote Similarity	NPC293458
0.6887	Remote Similarity	NPC300299
0.6882	Remote Similarity	NPC260075
0.6879	Remote Similarity	NPC2933
0.6875	Remote Similarity	NPC285381
0.6875	Remote Similarity	NPC122106
0.6871	Remote Similarity	NPC478079
0.687	Remote Similarity	NPC75496
0.6859	Remote Similarity	NPC136002
0.6857	Remote Similarity	NPC229484
0.6849	Remote Similarity	NPC472244
0.6849	Remote Similarity	NPC470343
0.6835	Remote Similarity	NPC57051
0.6829	Remote Similarity	NPC143457
0.6828	Remote Similarity	NPC254698
0.6824	Remote Similarity	NPC209389
0.6824	Remote Similarity	NPC150863
0.6821	Remote Similarity	NPC256288
0.6818	Remote Similarity	NPC207554
0.6818	Remote Similarity	NPC292675
0.681	Remote Similarity	NPC211525
0.681	Remote Similarity	NPC153694
0.6806	Remote Similarity	NPC475915
0.6805	Remote Similarity	NPC177261
0.6805	Remote Similarity	NPC476425
0.6795	Remote Similarity	NPC308197
0.679	Remote Similarity	NPC473297
0.6779	Remote Similarity	NPC472245
0.6779	Remote Similarity	NPC280807
0.6779	Remote Similarity	NPC314431
0.6778	Remote Similarity	NPC472540
0.6778	Remote Similarity	NPC470787
0.6778	Remote Similarity	NPC472539
0.6768	Remote Similarity	NPC310403
0.6768	Remote Similarity	NPC263709
0.6768	Remote Similarity	NPC97380
0.6768	Remote Similarity	NPC148468
0.6768	Remote Similarity	NPC243673
0.6768	Remote Similarity	NPC63210
0.6767	Remote Similarity	NPC291610
0.6759	Remote Similarity	NPC268534
0.6759	Remote Similarity	NPC39818
0.6753	Remote Similarity	NPC83214
0.6748	Remote Similarity	NPC469536
0.674	Remote Similarity	NPC472541
0.674	Remote Similarity	NPC472542
0.6736	Remote Similarity	NPC279385
0.6736	Remote Similarity	NPC179605
0.673	Remote Similarity	NPC212799
0.6725	Remote Similarity	NPC203202
0.6725	Remote Similarity	NPC264482
0.6725	Remote Similarity	NPC476441
0.6713	Remote Similarity	NPC228515
0.6703	Remote Similarity	NPC477179
0.669	Remote Similarity	NPC103292
0.6687	Remote Similarity	NPC472121
0.6687	Remote Similarity	NPC476231
0.6687	Remote Similarity	NPC286871
0.6687	Remote Similarity	NPC242000
0.6686	Remote Similarity	NPC472118
0.6667	Remote Similarity	NPC477178
0.6667	Remote Similarity	NPC477180
0.6667	Remote Similarity	NPC477181
0.6667	Remote Similarity	NPC472115
0.6667	Remote Similarity	NPC254850
0.6667	Remote Similarity	NPC472114
0.6649	Remote Similarity	NPC471436
0.6648	Remote Similarity	NPC307396
0.6648	Remote Similarity	NPC471199
0.6647	Remote Similarity	NPC99043
0.6647	Remote Similarity	NPC248462
0.6647	Remote Similarity	NPC6974
0.6647	Remote Similarity	NPC218594
0.6647	Remote Similarity	NPC271797
0.6647	Remote Similarity	NPC21174
0.6646	Remote Similarity	NPC318086
0.6631	Remote Similarity	NPC477173
0.6631	Remote Similarity	NPC470490
0.6631	Remote Similarity	NPC477174
0.6627	Remote Similarity	NPC201424
0.6621	Remote Similarity	NPC316582
0.6618	Remote Similarity	NPC473418
0.6607	Remote Similarity	NPC470069
0.6607	Remote Similarity	NPC52059
0.6596	Remote Similarity	NPC470488
0.6596	Remote Similarity	NPC187036
0.6592	Remote Similarity	NPC22689
0.6592	Remote Similarity	NPC105055
0.6581	Remote Similarity	NPC122553
0.6579	Remote Similarity	NPC473962
0.6577	Remote Similarity	NPC322433
0.6576	Remote Similarity	NPC106118
0.657	Remote Similarity	NPC329338
0.657	Remote Similarity	NPC469529
0.657	Remote Similarity	NPC469726
0.6568	Remote Similarity	NPC56233
0.6567	Remote Similarity	NPC326792
0.6561	Remote Similarity	NPC475259
0.6561	Remote Similarity	NPC471950
0.6561	Remote Similarity	NPC470491
0.6561	Remote Similarity	NPC471945
0.6556	Remote Similarity	NPC276430
0.6554	Remote Similarity	NPC133003
0.6548	Remote Similarity	NPC328270
0.6541	Remote Similarity	NPC470822
0.6534	Remote Similarity	NPC159963
0.6528	Remote Similarity	NPC192209
0.6526	Remote Similarity	NPC471951
0.6526	Remote Similarity	NPC471946
0.6524	Remote Similarity	NPC295021
0.6522	Remote Similarity	NPC20322
0.6519	Remote Similarity	NPC238499
0.6519	Remote Similarity	NPC471386
0.6513	Remote Similarity	NPC231382
0.6512	Remote Similarity	NPC21752
0.6512	Remote Similarity	NPC473743

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 NPC469560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	594
0.2-0.3	941
0.3-0.4	1782
0.4-0.5	3410
0.5-0.6	1881
0.6-0.7	326
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6566	Discontinued
0.7692	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5918	Discontinued
0.7647	Intermediate Similarity	NPD3248	Phase 1
0.7594	Intermediate Similarity	NPD5181	Approved
0.7594	Intermediate Similarity	NPD5179	Approved
0.7594	Intermediate Similarity	NPD5180	Approved
0.7586	Intermediate Similarity	NPD6318	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1064	Approved
0.7462	Intermediate Similarity	NPD1065	Approved
0.745	Intermediate Similarity	NPD3625	Discontinued
0.7413	Intermediate Similarity	NPD4549	Discontinued
0.7285	Intermediate Similarity	NPD6768	Approved
0.7273	Intermediate Similarity	NPD3240	Phase 2
0.7255	Intermediate Similarity	NPD5932	Phase 3
0.7255	Intermediate Similarity	NPD5931	Phase 3
0.7255	Intermediate Similarity	NPD5933	Phase 3
0.7248	Intermediate Similarity	NPD6358	Phase 2
0.7241	Intermediate Similarity	NPD5131	Approved
0.7233	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4116	Approved
0.7143	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2950	Approved
0.7095	Intermediate Similarity	NPD2949	Approved
0.708	Intermediate Similarity	NPD1175	Approved
0.7063	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1124	Approved
0.7042	Intermediate Similarity	NPD1123	Approved
0.7034	Intermediate Similarity	NPD2840	Approved
0.7032	Intermediate Similarity	NPD6017	Discontinued
0.7013	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2820	Phase 3
0.7007	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7072	Phase 2
0.6993	Remote Similarity	NPD2010	Phase 3
0.6986	Remote Similarity	NPD5993	Phase 1
0.6966	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1342	Approved
0.6959	Remote Similarity	NPD4783	Approved
0.6959	Remote Similarity	NPD4781	Approved
0.6954	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2365	Approved
0.6937	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1344	Phase 2
0.6928	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7633	Discontinued
0.6908	Remote Similarity	NPD6342	Discontinued
0.6899	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7578	Phase 2
0.6867	Remote Similarity	NPD1527	Phase 2
0.6863	Remote Similarity	NPD7254	Discontinued
0.6848	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6489	Phase 3
0.6846	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3387	Approved
0.6832	Remote Similarity	NPD2790	Discontinued
0.6824	Remote Similarity	NPD1781	Discontinued
0.6812	Remote Similarity	NPD2124	Approved
0.6803	Remote Similarity	NPD797	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1919	Approved
0.68	Remote Similarity	NPD1920	Approved
0.6795	Remote Similarity	NPD2129	Approved
0.6792	Remote Similarity	NPD4942	Approved
0.6786	Remote Similarity	NPD3551	Approved
0.6786	Remote Similarity	NPD3867	Phase 2
0.6784	Remote Similarity	NPD5840	Discontinued
0.6779	Remote Similarity	NPD8263	Discontinued
0.6767	Remote Similarity	NPD708	Approved
0.6767	Remote Similarity	NPD4803	Discontinued
0.6761	Remote Similarity	NPD5991	Approved
0.6761	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5990	Approved
0.6753	Remote Similarity	NPD7142	Discontinued
0.675	Remote Similarity	NPD5748	Phase 2
0.6747	Remote Similarity	NPD3790	Phase 2
0.6746	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2913	Approved
0.6714	Remote Similarity	NPD2914	Approved
0.6713	Remote Similarity	NPD6345	Approved
0.6713	Remote Similarity	NPD6343	Approved
0.6707	Remote Similarity	NPD8630	Approved
0.6691	Remote Similarity	NPD3545	Approved
0.6691	Remote Similarity	NPD3865	Approved
0.6691	Remote Similarity	NPD3546	Approved
0.6687	Remote Similarity	NPD4682	Phase 2
0.6667	Remote Similarity	NPD3549	Approved
0.6667	Remote Similarity	NPD6629	Discontinued
0.6667	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2791	Discontinued
0.6667	Remote Similarity	NPD3547	Approved
0.6667	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9541	Approved
0.6667	Remote Similarity	NPD9539	Approved
0.6667	Remote Similarity	NPD2508	Discontinued
0.6646	Remote Similarity	NPD1663	Discontinued
0.6646	Remote Similarity	NPD7487	Discontinued
0.6646	Remote Similarity	NPD2351	Discontinued
0.6642	Remote Similarity	NPD4115	Approved
0.6642	Remote Similarity	NPD4114	Approved
0.6624	Remote Similarity	NPD6512	Approved
0.6624	Remote Similarity	NPD6513	Approved
0.6623	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD8128	Discontinued
0.6611	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6043	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5184	Approved
0.6601	Remote Similarity	NPD7200	Approved
0.6601	Remote Similarity	NPD5182	Approved
0.6601	Remote Similarity	NPD5185	Approved
0.6582	Remote Similarity	NPD5024	Approved
0.6582	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5526	Phase 2
0.6582	Remote Similarity	NPD4430	Phase 2
0.6577	Remote Similarity	NPD9540	Approved
0.6575	Remote Similarity	NPD1079	Discontinued
0.6571	Remote Similarity	NPD1966	Approved
0.6567	Remote Similarity	NPD479	Approved
0.6566	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4393	Approved
0.6566	Remote Similarity	NPD33	Approved
0.6566	Remote Similarity	NPD7599	Phase 2
0.6562	Remote Similarity	NPD1524	Phase 1
0.6561	Remote Similarity	NPD2093	Discontinued
0.6561	Remote Similarity	NPD4461	Discontinued
0.6558	Remote Similarity	NPD2331	Discontinued
0.6556	Remote Similarity	NPD8240	Discontinued
0.6556	Remote Similarity	NPD4365	Phase 2
0.6552	Remote Similarity	NPD3076	Approved
0.6552	Remote Similarity	NPD3079	Approved
0.6552	Remote Similarity	NPD3077	Approved
0.6552	Remote Similarity	NPD3078	Approved
0.6549	Remote Similarity	NPD5629	Discontinued
0.6549	Remote Similarity	NPD5631	Phase 3
0.6547	Remote Similarity	NPD3581	Discontinued
0.6545	Remote Similarity	NPD6395	Phase 2
0.6545	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4178	Approved
0.6531	Remote Similarity	NPD4176	Approved
0.6531	Remote Similarity	NPD3624	Phase 2
0.6527	Remote Similarity	NPD7600	Phase 2
0.6522	Remote Similarity	NPD1054	Approved
0.6522	Remote Similarity	NPD4970	Phase 2
0.6522	Remote Similarity	NPD4968	Phase 2
0.6522	Remote Similarity	NPD4969	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD813	Approved
0.6519	Remote Similarity	NPD3482	Approved
0.6514	Remote Similarity	NPD3989	Phase 3
0.6513	Remote Similarity	NPD1619	Phase 3
0.6513	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2754	Discontinued
0.651	Remote Similarity	NPD2962	Approved
0.651	Remote Similarity	NPD2961	Approved
0.6507	Remote Similarity	NPD1299	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8060	Phase 1
0.6503	Remote Similarity	NPD1323	Discontinued
0.6497	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5600	Discontinued
0.6493	Remote Similarity	NPD742	Approved
0.6483	Remote Similarity	NPD5657	Phase 3
0.6481	Remote Similarity	NPD5941	Approved
0.6481	Remote Similarity	NPD5942	Approved
0.6478	Remote Similarity	NPD7082	Approved
0.6477	Remote Similarity	NPD3990	Phase 3
0.6474	Remote Similarity	NPD5318	Discontinued
0.6467	Remote Similarity	NPD1949	Approved
0.6467	Remote Similarity	NPD1950	Approved
0.6464	Remote Similarity	NPD1658	Discontinued
0.646	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6069	Approved
0.6458	Remote Similarity	NPD6070	Approved
0.6458	Remote Similarity	NPD7679	Phase 2
0.6454	Remote Similarity	NPD3001	Approved
0.6454	Remote Similarity	NPD2038	Approved
0.6454	Remote Similarity	NPD2999	Approved
0.6454	Remote Similarity	NPD2039	Approved
0.6452	Remote Similarity	NPD1410	Phase 1
0.6443	Remote Similarity	NPD7464	Phase 3
0.6438	Remote Similarity	NPD4043	Approved
0.6438	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7259	Approved
0.6438	Remote Similarity	NPD3481	Approved
0.6438	Remote Similarity	NPD4046	Approved
0.6433	Remote Similarity	NPD201	Phase 2
0.6433	Remote Similarity	NPD200	Phase 2

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