NPASS Compound

Structure

NPC25401 OpenBabel07101718292D 25 30 0 0 1 0 0 0 0 0999 V2000 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7323 1.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4497 -1.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 -0.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6792 -1.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4896 -0.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3492 -1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0647 -1.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3139 -0.6584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7191 -0.0027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1294 0.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4925 0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9804 1.7160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4349 -0.4757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2207 0.5853 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.7622 2.3395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0495 2.0814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 24 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 12 2 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 9 22 1 0 0 0 0 10 22 1 0 0 0 0 11 20 1 1 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 6 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 8 1 1 0 0 0 20 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.16
Volume:	338.319
LogP:	1.947
LogD:	1.499
LogS:	-3.831
# Rotatable Bonds:	2
TPSA:	54.43
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	6.001
Fsp3:	0.6
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:	-4.775
MDCK Permeability:	3.211124203517102e-05
Pgp-inhibitor:	0.558
Pgp-substrate:	0.866
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.289
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	49.85841751098633%
Volume Distribution (VD):	1.68
Pgp-substrate:	65.943359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.256
CYP1A2-substrate:	0.849
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.327
CYP3A4-substrate:	0.625

ADMET: Excretion

Clearance (CL):	9.935
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.928
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.309
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.572
Carcinogencity:	0.177
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC25401

Natural Product ID:	NPC25401
*Common Name:**	Melodinine D
IUPAC Name:	n.a.
Synonyms:	Melodinine D
Standard InCHIKey:	NYHQYHWNIWLUDO-ULKXNHMISA-N
Standard InCHI:	InChI=1S/C20H22N2O3/c1-11-20(25-11)13-7-9-22-10-8-19(18(20)22)12-5-3-4-6-14(12)21-16(19)15(13)17(23)24-2/h3-6,11,13,18,21H,7-10H2,1-2H3/t11-,13+,18-,19+,20+/m0/s1
SMILES:	COC(=O)C1=C2Nc3c([C@]42[C@H]2[C@@]5([C@@H]1CCN2CC4)O[C@H]5C)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087384
PubChem CID:	44626859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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[479469]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[479469]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[479469]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[479469]

☑ 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 NPC25401 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	264
0.1-0.2	1139
0.2-0.3	3482
0.3-0.4	13220
0.4-0.5	18759
0.5-0.6	4847
0.6-0.7	802
0.7-0.8	150
0.8-0.85	21
0.85-0.9	8
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC159963
0.9477	High Similarity	NPC14994
0.929	High Similarity	NPC203202
0.929	High Similarity	NPC264482
0.9012	High Similarity	NPC186669
0.896	High Similarity	NPC218594
0.896	High Similarity	NPC6974
0.896	High Similarity	NPC99043
0.8698	High Similarity	NPC248117
0.8652	High Similarity	NPC97584
0.8639	High Similarity	NPC193410
0.858	High Similarity	NPC61013
0.8555	High Similarity	NPC223595
0.8555	High Similarity	NPC167724
0.8555	High Similarity	NPC224970
0.8363	Intermediate Similarity	NPC123241
0.8324	Intermediate Similarity	NPC293458
0.8306	Intermediate Similarity	NPC181928
0.822	Intermediate Similarity	NPC1464
0.8208	Intermediate Similarity	NPC36495
0.8191	Intermediate Similarity	NPC77777
0.8187	Intermediate Similarity	NPC195787
0.8187	Intermediate Similarity	NPC246140
0.8156	Intermediate Similarity	NPC469726
0.8156	Intermediate Similarity	NPC329338
0.8141	Intermediate Similarity	NPC195636
0.8118	Intermediate Similarity	NPC473298
0.8042	Intermediate Similarity	NPC34717
0.802	Intermediate Similarity	NPC476069
0.8011	Intermediate Similarity	NPC282339
0.8011	Intermediate Similarity	NPC99632
0.7958	Intermediate Similarity	NPC90967
0.7864	Intermediate Similarity	NPC19175
0.7857	Intermediate Similarity	NPC87714
0.7831	Intermediate Similarity	NPC5630
0.781	Intermediate Similarity	NPC139373
0.7799	Intermediate Similarity	NPC223242
0.7737	Intermediate Similarity	NPC22689
0.7737	Intermediate Similarity	NPC105055
0.7732	Intermediate Similarity	NPC132874
0.7732	Intermediate Similarity	NPC138615
0.7732	Intermediate Similarity	NPC265642
0.7732	Intermediate Similarity	NPC218733
0.7713	Intermediate Similarity	NPC52262
0.7705	Intermediate Similarity	NPC139085
0.7705	Intermediate Similarity	NPC251212
0.7705	Intermediate Similarity	NPC214626
0.7696	Intermediate Similarity	NPC203628
0.7696	Intermediate Similarity	NPC22476
0.7685	Intermediate Similarity	NPC189661
0.7654	Intermediate Similarity	NPC225319
0.7628	Intermediate Similarity	NPC301501
0.7614	Intermediate Similarity	NPC471512
0.7609	Intermediate Similarity	NPC276993
0.7609	Intermediate Similarity	NPC298851
0.7609	Intermediate Similarity	NPC21752
0.7609	Intermediate Similarity	NPC181138
0.7609	Intermediate Similarity	NPC210415
0.7609	Intermediate Similarity	NPC293255
0.7582	Intermediate Similarity	NPC214960
0.7582	Intermediate Similarity	NPC279527
0.7581	Intermediate Similarity	NPC260075
0.7581	Intermediate Similarity	NPC131977
0.7556	Intermediate Similarity	NPC474058
0.7548	Intermediate Similarity	NPC128476
0.7538	Intermediate Similarity	NPC303214
0.7535	Intermediate Similarity	NPC291173
0.7514	Intermediate Similarity	NPC285622
0.7512	Intermediate Similarity	NPC469450
0.7459	Intermediate Similarity	NPC309531
0.7459	Intermediate Similarity	NPC472102
0.7444	Intermediate Similarity	NPC113946
0.7443	Intermediate Similarity	NPC469452
0.7443	Intermediate Similarity	NPC469451
0.7441	Intermediate Similarity	NPC231924
0.7437	Intermediate Similarity	NPC232600
0.7413	Intermediate Similarity	NPC475147
0.7391	Intermediate Similarity	NPC234772
0.7376	Intermediate Similarity	NPC329932
0.7373	Intermediate Similarity	NPC154922
0.7354	Intermediate Similarity	NPC321211
0.7353	Intermediate Similarity	NPC475133
0.7344	Intermediate Similarity	NPC322621
0.7333	Intermediate Similarity	NPC161827
0.7326	Intermediate Similarity	NPC96901
0.7322	Intermediate Similarity	NPC472101
0.7322	Intermediate Similarity	NPC472120
0.7322	Intermediate Similarity	NPC286871
0.731	Intermediate Similarity	NPC221687
0.7297	Intermediate Similarity	NPC472114
0.7297	Intermediate Similarity	NPC472115
0.7285	Intermediate Similarity	NPC469722
0.7264	Intermediate Similarity	NPC469732
0.7243	Intermediate Similarity	NPC472106
0.7234	Intermediate Similarity	NPC476425
0.7234	Intermediate Similarity	NPC177261
0.7233	Intermediate Similarity	NPC269449
0.7232	Intermediate Similarity	NPC264589
0.7228	Intermediate Similarity	NPC176983
0.7228	Intermediate Similarity	NPC472117
0.7214	Intermediate Similarity	NPC475489
0.7214	Intermediate Similarity	NPC138830
0.7213	Intermediate Similarity	NPC63210
0.7213	Intermediate Similarity	NPC97380
0.7213	Intermediate Similarity	NPC243673
0.7213	Intermediate Similarity	NPC310403
0.7213	Intermediate Similarity	NPC263709
0.7213	Intermediate Similarity	NPC148468
0.7212	Intermediate Similarity	NPC472291
0.7209	Intermediate Similarity	NPC473458
0.7207	Intermediate Similarity	NPC113455
0.7188	Intermediate Similarity	NPC475962
0.7186	Intermediate Similarity	NPC97100
0.7186	Intermediate Similarity	NPC473375
0.7182	Intermediate Similarity	NPC478076
0.7167	Intermediate Similarity	NPC475763
0.7167	Intermediate Similarity	NPC243756
0.7165	Intermediate Similarity	NPC259626
0.7165	Intermediate Similarity	NPC49184
0.7163	Intermediate Similarity	NPC119722
0.7151	Intermediate Similarity	NPC470069
0.7151	Intermediate Similarity	NPC52059
0.715	Intermediate Similarity	NPC477159
0.7143	Intermediate Similarity	NPC477397
0.7135	Intermediate Similarity	NPC472121
0.713	Intermediate Similarity	NPC471513
0.7129	Intermediate Similarity	NPC214428
0.7128	Intermediate Similarity	NPC472118
0.7128	Intermediate Similarity	NPC473615
0.7116	Intermediate Similarity	NPC477394
0.7114	Intermediate Similarity	NPC100863
0.7113	Intermediate Similarity	NPC2933
0.7111	Intermediate Similarity	NPC120239
0.7109	Intermediate Similarity	NPC473837
0.7104	Intermediate Similarity	NPC29285
0.7092	Intermediate Similarity	NPC229484
0.7092	Intermediate Similarity	NPC21425
0.7091	Intermediate Similarity	NPC160113
0.7091	Intermediate Similarity	NPC476220
0.7081	Intermediate Similarity	NPC201424
0.7077	Intermediate Similarity	NPC472209
0.7068	Intermediate Similarity	NPC476441
0.7065	Intermediate Similarity	NPC162440
0.7065	Intermediate Similarity	NPC153694
0.7065	Intermediate Similarity	NPC211525
0.7062	Intermediate Similarity	NPC256288
0.7056	Intermediate Similarity	NPC292675
0.7044	Intermediate Similarity	NPC67904
0.7043	Intermediate Similarity	NPC85651
0.7039	Intermediate Similarity	NPC277350
0.7037	Intermediate Similarity	NPC469915
0.7031	Intermediate Similarity	NPC476326
0.7017	Intermediate Similarity	NPC473329
0.7	Intermediate Similarity	NPC127996
0.6996	Remote Similarity	NPC151171
0.6979	Remote Similarity	NPC129624
0.6965	Remote Similarity	NPC198205
0.6965	Remote Similarity	NPC21483
0.6964	Remote Similarity	NPC476258
0.6964	Remote Similarity	NPC304837
0.6963	Remote Similarity	NPC288110
0.6963	Remote Similarity	NPC223590
0.6961	Remote Similarity	NPC312870
0.6961	Remote Similarity	NPC199851
0.6961	Remote Similarity	NPC254240
0.6961	Remote Similarity	NPC294909
0.6961	Remote Similarity	NPC128265
0.6948	Remote Similarity	NPC471197
0.6948	Remote Similarity	NPC126556
0.6946	Remote Similarity	NPC112752
0.6946	Remote Similarity	NPC311054
0.694	Remote Similarity	NPC122106
0.6931	Remote Similarity	NPC245916
0.6931	Remote Similarity	NPC278887
0.6923	Remote Similarity	NPC478075
0.6919	Remote Similarity	NPC63370
0.6919	Remote Similarity	NPC36836
0.6916	Remote Similarity	NPC471198
0.6915	Remote Similarity	NPC313757
0.6915	Remote Similarity	NPC470485
0.6908	Remote Similarity	NPC329833
0.6903	Remote Similarity	NPC477395
0.6898	Remote Similarity	NPC315368
0.6897	Remote Similarity	NPC198390
0.6893	Remote Similarity	NPC162730
0.6893	Remote Similarity	NPC475223
0.689	Remote Similarity	NPC285192
0.6885	Remote Similarity	NPC314223
0.6884	Remote Similarity	NPC316405
0.6884	Remote Similarity	NPC284706
0.6878	Remote Similarity	NPC473781
0.6878	Remote Similarity	NPC470631
0.6878	Remote Similarity	NPC35390
0.686	Remote Similarity	NPC475448
0.686	Remote Similarity	NPC246983
0.6857	Remote Similarity	NPC477160
0.6849	Remote Similarity	NPC476436
0.6849	Remote Similarity	NPC472762
0.6847	Remote Similarity	NPC475316
0.6847	Remote Similarity	NPC473486

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 NPC25401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	490
0.2-0.3	714
0.3-0.4	1435
0.4-0.5	3727
0.5-0.6	2326
0.6-0.7	284
0.7-0.8	10
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
0.7151	Intermediate Similarity	NPD7035	Approved
0.7151	Intermediate Similarity	NPD7036	Phase 3
0.7095	Intermediate Similarity	NPD1801	Approved
0.7095	Intermediate Similarity	NPD1802	Approved
0.6961	Remote Similarity	NPD4501	Approved
0.6961	Remote Similarity	NPD4500	Approved
0.6919	Remote Similarity	NPD6571	Approved
0.6919	Remote Similarity	NPD6570	Approved
0.6851	Remote Similarity	NPD4041	Approved
0.6845	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3828	Approved
0.6802	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5184	Approved
0.68	Remote Similarity	NPD5182	Approved
0.68	Remote Similarity	NPD5185	Approved
0.6796	Remote Similarity	NPD6805	Discontinued
0.6788	Remote Similarity	NPD5997	Discontinued
0.6757	Remote Similarity	NPD3399	Approved
0.6754	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7940	Phase 3
0.6742	Remote Similarity	NPD1109	Approved
0.6742	Remote Similarity	NPD1110	Approved
0.6742	Remote Similarity	NPD3170	Approved
0.674	Remote Similarity	NPD7487	Discontinued
0.674	Remote Similarity	NPD2435	Approved
0.6737	Remote Similarity	NPD8008	Approved
0.6737	Remote Similarity	NPD8007	Approved
0.6735	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7244	Discontinued
0.6717	Remote Similarity	NPD8281	Discontinued
0.6685	Remote Similarity	NPD2670	Approved
0.6685	Remote Similarity	NPD7528	Approved
0.6667	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6770	Approved
0.6651	Remote Similarity	NPD4082	Approved
0.665	Remote Similarity	NPD7775	Approved
0.6649	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4493	Discontinued
0.6631	Remote Similarity	NPD4121	Phase 3
0.6631	Remote Similarity	NPD4120	Approved
0.6613	Remote Similarity	NPD7606	Phase 3
0.6605	Remote Similarity	NPD4492	Approved
0.6605	Remote Similarity	NPD4494	Approved
0.6603	Remote Similarity	NPD6238	Discontinued
0.6601	Remote Similarity	NPD4499	Approved
0.6596	Remote Similarity	NPD5743	Approved
0.6596	Remote Similarity	NPD5741	Approved
0.6596	Remote Similarity	NPD5742	Approved
0.6583	Remote Similarity	NPD3471	Approved
0.6583	Remote Similarity	NPD3470	Approved
0.6566	Remote Similarity	NPD7881	Approved
0.656	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7478	Approved
0.654	Remote Similarity	NPD7205	Discontinued
0.6526	Remote Similarity	NPD4596	Phase 1
0.652	Remote Similarity	NPD6625	Approved
0.652	Remote Similarity	NPD5928	Phase 1
0.6513	Remote Similarity	NPD5186	Approved
0.6513	Remote Similarity	NPD5183	Approved
0.6513	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5942	Approved
0.6505	Remote Similarity	NPD5941	Approved
0.65	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD2510	Approved
0.6495	Remote Similarity	NPD2509	Approved
0.6489	Remote Similarity	NPD2948	Discontinued
0.6488	Remote Similarity	NPD5504	Discontinued
0.6486	Remote Similarity	NPD4607	Approved
0.648	Remote Similarity	NPD2431	Approved
0.648	Remote Similarity	NPD2432	Approved
0.6476	Remote Similarity	NPD4600	Approved
0.6476	Remote Similarity	NPD4601	Approved
0.6471	Remote Similarity	NPD3437	Discontinued
0.6468	Remote Similarity	NPD7962	Phase 2
0.6462	Remote Similarity	NPD2037	Approved
0.6462	Remote Similarity	NPD2681	Approved
0.6462	Remote Similarity	NPD2680	Approved
0.6458	Remote Similarity	NPD7600	Phase 2
0.6452	Remote Similarity	NPD3352	Approved
0.645	Remote Similarity	NPD4329	Approved
0.645	Remote Similarity	NPD4330	Approved
0.6448	Remote Similarity	NPD2923	Approved
0.6447	Remote Similarity	NPD7854	Phase 2
0.644	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3893	Discontinued
0.6432	Remote Similarity	NPD7688	Phase 1
0.6432	Remote Similarity	NPD7295	Approved
0.6432	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6185	Discontinued
0.6429	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4455	Discontinued
0.6419	Remote Similarity	NPD4022	Approved
0.6419	Remote Similarity	NPD3472	Approved
0.6414	Remote Similarity	NPD3422	Phase 3
0.6414	Remote Similarity	NPD5466	Approved
0.6414	Remote Similarity	NPD3423	Phase 2
0.6411	Remote Similarity	NPD5003	Discontinued
0.6406	Remote Similarity	NPD7599	Phase 2
0.6396	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3006	Discontinued
0.6389	Remote Similarity	NPD4506	Discontinued
0.6384	Remote Similarity	NPD3912	Discontinued
0.6383	Remote Similarity	NPD4513	Discontinued
0.6378	Remote Similarity	NPD2454	Approved
0.6378	Remote Similarity	NPD2455	Approved
0.6376	Remote Similarity	NPD3888	Discontinued
0.6369	Remote Similarity	NPD3087	Approved
0.6369	Remote Similarity	NPD3616	Approved
0.6369	Remote Similarity	NPD3089	Approved
0.6369	Remote Similarity	NPD2571	Approved
0.6369	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2573	Approved
0.6369	Remote Similarity	NPD2570	Approved
0.6369	Remote Similarity	NPD3615	Approved
0.6369	Remote Similarity	NPD4745	Approved
0.6369	Remote Similarity	NPD2566	Approved
0.6369	Remote Similarity	NPD3090	Approved
0.6369	Remote Similarity	NPD2574	Discontinued
0.6369	Remote Similarity	NPD3614	Approved
0.6369	Remote Similarity	NPD4746	Phase 3
0.6369	Remote Similarity	NPD3088	Approved
0.6364	Remote Similarity	NPD6758	Approved
0.6359	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5430	Discontinued
0.6359	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3372	Discontinued
0.6355	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3436	Approved
0.635	Remote Similarity	NPD3792	Approved
0.635	Remote Similarity	NPD5600	Discontinued
0.6343	Remote Similarity	NPD4859	Phase 1
0.6343	Remote Similarity	NPD8399	Phase 1
0.6343	Remote Similarity	NPD8423	Phase 2
0.633	Remote Similarity	NPD1945	Phase 1
0.6329	Remote Similarity	NPD6659	Phase 2
0.6327	Remote Similarity	NPD7186	Phase 3
0.6324	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2567	Approved
0.6319	Remote Similarity	NPD2569	Approved
0.6313	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD3790	Phase 2
0.6308	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3625	Discontinued
0.6303	Remote Similarity	NPD4420	Approved
0.6303	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD1663	Discontinued
0.6302	Remote Similarity	NPD7105	Phase 1
0.6301	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4684	Phase 3
0.6298	Remote Similarity	NPD4686	Approved
0.6298	Remote Similarity	NPD4685	Phase 3
0.6294	Remote Similarity	NPD2404	Discontinued
0.6289	Remote Similarity	NPD2506	Approved
0.6287	Remote Similarity	NPD6878	Phase 2
0.6287	Remote Similarity	NPD6879	Phase 2
0.6286	Remote Similarity	NPD5582	Discontinued
0.6283	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.628	Remote Similarity	NPD2564	Approved
0.628	Remote Similarity	NPD2565	Phase 2
0.628	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1294	Discontinued
0.6279	Remote Similarity	NPD56	Approved
0.6279	Remote Similarity	NPD8283	Approved
0.6279	Remote Similarity	NPD8282	Approved
0.6269	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5006	Approved
0.6262	Remote Similarity	NPD5005	Approved
0.6262	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6017	Discontinued
0.6256	Remote Similarity	NPD3435	Discontinued
0.625	Remote Similarity	NPD1093	Approved
0.625	Remote Similarity	NPD1092	Approved
0.625	Remote Similarity	NPD5042	Phase 1
0.625	Remote Similarity	NPD5891	Approved
0.6245	Remote Similarity	NPD6199	Discontinued
0.6244	Remote Similarity	NPD6557	Phase 2
0.6243	Remote Similarity	NPD4888	Discontinued
0.6238	Remote Similarity	NPD4602	Approved
0.6238	Remote Similarity	NPD3782	Discontinued
0.6237	Remote Similarity	NPD7082	Approved
0.6237	Remote Similarity	NPD2820	Phase 3
0.6233	Remote Similarity	NPD6176	Phase 1
0.6231	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5318	Discontinued
0.623	Remote Similarity	NPD7708	Approved
0.6226	Remote Similarity	NPD4668	Phase 2
0.6219	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3393	Approved
0.6216	Remote Similarity	NPD3394	Approved
0.6216	Remote Similarity	NPD3389	Approved
0.6212	Remote Similarity	NPD2249	Approved
0.6212	Remote Similarity	NPD3468	Approved
0.6212	Remote Similarity	NPD2247	Approved

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