NPASS Compound

Structure

CID66936 OpenBabel06191715402D 39 44 0 0 1 0 0 0 0 0999 V2000 2.5924 -4.2015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1912 -5.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0370 1.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9271 4.0697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9271 4.0697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5611 0.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3911 -4.5151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1978 2.4044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1923 2.5089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2931 1.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2089 1.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7801 1.6999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1710 2.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 3.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2931 2.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4271 1.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 0.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5722 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5979 -4.3061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1710 1.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3789 0.6818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 1.2037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3734 0.7863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1654 -1.8790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5611 2.7037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0101 -3.4971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5722 -2.7926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4169 -2.5835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0370 -0.7963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4271 3.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5611 1.7037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1710 -0.2963 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0156 -3.6016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7801 -0.1272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8291 -1.7745 0.0000 N 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 -1.5667 -2.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4114 -2.4790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 2 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 7 34 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 22 2 0 0 0 0 12 24 2 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 23 1 0 0 0 0 18 33 1 0 0 0 0 19 35 1 0 0 0 0 19 37 2 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 32 1 6 0 0 0 24 35 1 0 0 0 0 25 18 1 6 0 0 0 25 28 1 0 0 0 0 25 36 1 0 0 0 0 26 31 1 0 0 0 0 26 32 1 6 0 0 0 27 20 1 6 0 0 0 27 29 1 0 0 0 0 27 34 1 0 0 0 0 28 34 1 0 0 0 0 28 38 2 0 0 0 0 29 36 1 0 0 0 0 29 39 2 0 0 0 0 30 33 1 1 0 0 0 30 35 1 0 0 0 0 30 36 1 0 0 0 0 32 6 1 6 0 0 0 33 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	531.35
Volume:	568.891
LogP:	5.935
LogD:	4.036
LogS:	-5.907
# Rotatable Bonds:	4
TPSA:	60.93
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	5.085
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.077
MDCK Permeability:	3.0445216907537542e-05
Pgp-inhibitor:	0.72
Pgp-substrate:	0.416
Human Intestinal Absorption (HIA):	0.316
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	69.30720520019531%
Volume Distribution (VD):	0.862
Pgp-substrate:	14.704368591308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.558
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	5.936
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.802
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.664
Carcinogencity:	0.785
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC66936

Natural Product ID:	NPC66936
*Common Name:**	Drimentine H
IUPAC Name:	n.a.
Synonyms:	Drimentine H
Standard InCHIKey:	ITMWMZIGMMDMQK-WHYFKYNSSA-N
Standard InCHI:	InChI=1S/C33H45N3O3/c1-20(2)27-29(39)36-25(28(38)34(27)7)18-33(22-11-8-9-12-24(22)35(19-37)30(33)36)17-23-21(3)13-14-26-31(4,5)15-10-16-32(23,26)6/h8-9,11-12,19-20,23,25-27,30H,3,10,13-18H2,1-2,4-7H3/t23-,25-,26-,27-,30-,32+,33-/m0/s1
SMILES:	CC(C)[C@H]1C(=O)N2[C@@H](C[C@@]3(C[C@H]4C(=C)CC[C@H]5C(C)(C)CCC[C@]45C)c4ccccc4N(C=O)[C@@H]23)C(=O)N1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333538
PubChem CID:	71665547
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO40602	Streptomyces sp. CHQ-64	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23547884]
NPO40602	Streptomyces sp. CHQ-64	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28418245]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[463117]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[463117]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[463117]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[463117]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[463117]

☑ 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 NPC66936 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	346
0.1-0.2	1759
0.2-0.3	8217
0.3-0.4	23350
0.4-0.5	6372
0.5-0.6	2210
0.6-0.7	344
0.7-0.8	91
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9257	High Similarity	NPC222029
0.8693	High Similarity	NPC276085
0.8671	High Similarity	NPC471123
0.8438	Intermediate Similarity	NPC242269
0.8299	Intermediate Similarity	NPC469560
0.8153	Intermediate Similarity	NPC104345
0.7935	Intermediate Similarity	NPC109787
0.7771	Intermediate Similarity	NPC285622
0.7716	Intermediate Similarity	NPC225319
0.7712	Intermediate Similarity	NPC186284
0.7712	Intermediate Similarity	NPC22082
0.7697	Intermediate Similarity	NPC63047
0.7697	Intermediate Similarity	NPC475248
0.7658	Intermediate Similarity	NPC473329
0.7654	Intermediate Similarity	NPC471122
0.7647	Intermediate Similarity	NPC130251
0.7576	Intermediate Similarity	NPC471124
0.75	Intermediate Similarity	NPC68650
0.75	Intermediate Similarity	NPC128582
0.7485	Intermediate Similarity	NPC113946
0.7455	Intermediate Similarity	NPC469741
0.7455	Intermediate Similarity	NPC282339
0.7455	Intermediate Similarity	NPC99632
0.7451	Intermediate Similarity	NPC267508
0.7442	Intermediate Similarity	NPC286994
0.7372	Intermediate Similarity	NPC301760
0.7371	Intermediate Similarity	NPC307396
0.7353	Intermediate Similarity	NPC214626
0.7353	Intermediate Similarity	NPC139085
0.7353	Intermediate Similarity	NPC251212
0.7301	Intermediate Similarity	NPC478076
0.7284	Intermediate Similarity	NPC243756
0.7278	Intermediate Similarity	NPC469537
0.7263	Intermediate Similarity	NPC276430
0.7262	Intermediate Similarity	NPC472106
0.7261	Intermediate Similarity	NPC470301
0.7246	Intermediate Similarity	NPC472117
0.7246	Intermediate Similarity	NPC472101
0.7246	Intermediate Similarity	NPC472120
0.7243	Intermediate Similarity	NPC471436
0.7219	Intermediate Similarity	NPC279527
0.7219	Intermediate Similarity	NPC214960
0.7205	Intermediate Similarity	NPC212799
0.7193	Intermediate Similarity	NPC355
0.7186	Intermediate Similarity	NPC309531
0.7186	Intermediate Similarity	NPC248117
0.7186	Intermediate Similarity	NPC472102
0.7178	Intermediate Similarity	NPC154602
0.7175	Intermediate Similarity	NPC259626
0.7158	Intermediate Similarity	NPC472542
0.7158	Intermediate Similarity	NPC472541
0.7151	Intermediate Similarity	NPC473743
0.7143	Intermediate Similarity	NPC471950
0.7143	Intermediate Similarity	NPC471945
0.7126	Intermediate Similarity	NPC193410
0.7119	Intermediate Similarity	NPC2933
0.7105	Intermediate Similarity	NPC471946
0.7105	Intermediate Similarity	NPC471951
0.7104	Intermediate Similarity	NPC472540
0.7104	Intermediate Similarity	NPC470787
0.7104	Intermediate Similarity	NPC472539
0.7066	Intermediate Similarity	NPC61013
0.7062	Intermediate Similarity	NPC256288
0.7056	Intermediate Similarity	NPC292675
0.7053	Intermediate Similarity	NPC475259
0.7053	Intermediate Similarity	NPC470491
0.7052	Intermediate Similarity	NPC96901
0.7052	Intermediate Similarity	NPC161861
0.703	Intermediate Similarity	NPC122106
0.7029	Intermediate Similarity	NPC260075
0.7024	Intermediate Similarity	NPC36495
0.7021	Intermediate Similarity	NPC477179
0.7011	Intermediate Similarity	NPC470548
0.7006	Intermediate Similarity	NPC29285
0.7	Intermediate Similarity	NPC229484
0.6984	Remote Similarity	NPC477178
0.6984	Remote Similarity	NPC477181
0.6984	Remote Similarity	NPC477180
0.6984	Remote Similarity	NPC254850
0.6982	Remote Similarity	NPC201424
0.6981	Remote Similarity	NPC315051
0.698	Remote Similarity	NPC475915
0.6973	Remote Similarity	NPC471199
0.6973	Remote Similarity	NPC162440
0.6947	Remote Similarity	NPC477174
0.6947	Remote Similarity	NPC477173
0.6947	Remote Similarity	NPC470490
0.6944	Remote Similarity	NPC473615
0.6941	Remote Similarity	NPC194881
0.6928	Remote Similarity	NPC145754
0.6928	Remote Similarity	NPC117032
0.6928	Remote Similarity	NPC285381
0.6923	Remote Similarity	NPC473298
0.6911	Remote Similarity	NPC470488
0.6905	Remote Similarity	NPC469536
0.6898	Remote Similarity	NPC106118
0.6891	Remote Similarity	NPC475359
0.6891	Remote Similarity	NPC191817
0.6879	Remote Similarity	NPC223595
0.6879	Remote Similarity	NPC167724
0.6879	Remote Similarity	NPC224970
0.6864	Remote Similarity	NPC123241
0.6859	Remote Similarity	NPC473962
0.6842	Remote Similarity	NPC286871
0.6839	Remote Similarity	NPC472118
0.6832	Remote Similarity	NPC471164
0.6831	Remote Similarity	NPC22689
0.6831	Remote Similarity	NPC105055
0.6829	Remote Similarity	NPC469735
0.6829	Remote Similarity	NPC264589
0.6821	Remote Similarity	NPC472115
0.6821	Remote Similarity	NPC472114
0.6809	Remote Similarity	NPC473418
0.6807	Remote Similarity	NPC318086
0.6803	Remote Similarity	NPC473573
0.6797	Remote Similarity	NPC79698
0.6788	Remote Similarity	NPC469740
0.6784	Remote Similarity	NPC315368
0.678	Remote Similarity	NPC203202
0.678	Remote Similarity	NPC264482
0.6772	Remote Similarity	NPC162417
0.6772	Remote Similarity	NPC316104
0.6761	Remote Similarity	NPC476425
0.6757	Remote Similarity	NPC471386
0.6753	Remote Similarity	NPC252794
0.6744	Remote Similarity	NPC176983
0.6744	Remote Similarity	NPC293458
0.6743	Remote Similarity	NPC469915
0.6739	Remote Similarity	NPC473569
0.6721	Remote Similarity	NPC181928
0.6719	Remote Similarity	NPC470489
0.671	Remote Similarity	NPC478079
0.6686	Remote Similarity	NPC474058
0.6685	Remote Similarity	NPC476441
0.6667	Remote Similarity	NPC475420
0.6667	Remote Similarity	NPC177261
0.6667	Remote Similarity	NPC209389
0.6667	Remote Similarity	NPC264580
0.6667	Remote Similarity	NPC141612
0.6667	Remote Similarity	NPC17273
0.6667	Remote Similarity	NPC206592
0.6667	Remote Similarity	NPC135601
0.6647	Remote Similarity	NPC473297
0.6646	Remote Similarity	NPC53044
0.6633	Remote Similarity	NPC470731
0.6632	Remote Similarity	NPC329833
0.6612	Remote Similarity	NPC52262
0.6611	Remote Similarity	NPC6974
0.6611	Remote Similarity	NPC99043
0.6611	Remote Similarity	NPC218594
0.6597	Remote Similarity	NPC67904
0.6597	Remote Similarity	NPC138830
0.6596	Remote Similarity	NPC34717
0.6596	Remote Similarity	NPC221687
0.6593	Remote Similarity	NPC470205
0.659	Remote Similarity	NPC143457
0.6588	Remote Similarity	NPC295021
0.6588	Remote Similarity	NPC200743
0.6582	Remote Similarity	NPC126458
0.658	Remote Similarity	NPC295548
0.6575	Remote Similarity	NPC11149
0.6573	Remote Similarity	NPC473880
0.6568	Remote Similarity	NPC475763
0.6564	Remote Similarity	NPC472538
0.6552	Remote Similarity	NPC474896
0.655	Remote Similarity	NPC470732
0.6541	Remote Similarity	NPC21425
0.6536	Remote Similarity	NPC469726
0.6536	Remote Similarity	NPC329338
0.6536	Remote Similarity	NPC475097
0.6533	Remote Similarity	NPC471663
0.652	Remote Similarity	NPC31097
0.6519	Remote Similarity	NPC187231
0.6514	Remote Similarity	NPC328270
0.6513	Remote Similarity	NPC226143
0.6513	Remote Similarity	NPC225400
0.651	Remote Similarity	NPC475489
0.6506	Remote Similarity	NPC311330
0.6488	Remote Similarity	NPC254798
0.6484	Remote Similarity	NPC91179
0.648	Remote Similarity	NPC470786
0.648	Remote Similarity	NPC471155
0.6479	Remote Similarity	NPC291610
0.6471	Remote Similarity	NPC161956
0.6471	Remote Similarity	NPC316582
0.6471	Remote Similarity	NPC258531
0.6471	Remote Similarity	NPC112373
0.6464	Remote Similarity	NPC476326
0.6463	Remote Similarity	NPC243162
0.6463	Remote Similarity	NPC207554
0.6456	Remote Similarity	NPC473322
0.6453	Remote Similarity	NPC161827
0.645	Remote Similarity	NPC473006
0.6447	Remote Similarity	NPC285192
0.6447	Remote Similarity	NPC228515
0.6447	Remote Similarity	NPC270241
0.644	Remote Similarity	NPC90967
0.6439	Remote Similarity	NPC253987
0.6432	Remote Similarity	NPC133003
0.6429	Remote Similarity	NPC257490

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 NPC66936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	546
0.2-0.3	818
0.3-0.4	2047
0.4-0.5	3493
0.5-0.6	1759
0.6-0.7	263
0.7-0.8	19
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
0.7702	Intermediate Similarity	NPD8630	Approved
0.7639	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6318	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8240	Discontinued
0.7261	Intermediate Similarity	NPD3625	Discontinued
0.7254	Intermediate Similarity	NPD5179	Approved
0.7254	Intermediate Similarity	NPD5181	Approved
0.7254	Intermediate Similarity	NPD5180	Approved
0.7215	Intermediate Similarity	NPD6566	Discontinued
0.7203	Intermediate Similarity	NPD3551	Approved
0.72	Intermediate Similarity	NPD3240	Phase 2
0.7179	Intermediate Similarity	NPD6358	Phase 2
0.7143	Intermediate Similarity	NPD7578	Phase 2
0.7126	Intermediate Similarity	NPD7599	Phase 2
0.7125	Intermediate Similarity	NPD5918	Discontinued
0.7115	Intermediate Similarity	NPD6102	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7679	Phase 2
0.7099	Intermediate Similarity	NPD7794	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5931	Phase 3
0.7081	Intermediate Similarity	NPD5932	Phase 3
0.7081	Intermediate Similarity	NPD5933	Phase 3
0.7066	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6768	Approved
0.6994	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2790	Discontinued
0.6982	Remote Similarity	NPD7600	Phase 2
0.6981	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8263	Discontinued
0.6948	Remote Similarity	NPD5131	Approved
0.6937	Remote Similarity	NPD2010	Phase 3
0.6928	Remote Similarity	NPD3248	Phase 1
0.6928	Remote Similarity	NPD5993	Phase 1
0.6918	Remote Similarity	NPD7254	Discontinued
0.6908	Remote Similarity	NPD8128	Discontinued
0.6897	Remote Similarity	NPD2914	Approved
0.6897	Remote Similarity	NPD2913	Approved
0.6853	Remote Similarity	NPD4116	Approved
0.6826	Remote Similarity	NPD8402	Approved
0.6826	Remote Similarity	NPD8401	Approved
0.6826	Remote Similarity	NPD8400	Approved
0.6813	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7142	Discontinued
0.681	Remote Similarity	NPD7487	Discontinued
0.68	Remote Similarity	NPD6806	Phase 1
0.6797	Remote Similarity	NPD6792	Phase 3
0.6797	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6489	Phase 3
0.6783	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6345	Approved
0.6779	Remote Similarity	NPD6343	Approved
0.6765	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6070	Approved
0.6757	Remote Similarity	NPD6069	Approved
0.6755	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2840	Approved
0.6748	Remote Similarity	NPD5024	Approved
0.6748	Remote Similarity	NPD5526	Phase 2
0.6748	Remote Similarity	NPD2820	Phase 3
0.6748	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5941	Approved
0.6747	Remote Similarity	NPD5942	Approved
0.6747	Remote Similarity	NPD4682	Phase 2
0.6747	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7633	Discontinued
0.6735	Remote Similarity	NPD5629	Discontinued
0.6732	Remote Similarity	NPD3549	Approved
0.6732	Remote Similarity	NPD3547	Approved
0.6732	Remote Similarity	NPD7464	Phase 3
0.6732	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5990	Approved
0.6711	Remote Similarity	NPD5991	Approved
0.6709	Remote Similarity	NPD2949	Approved
0.6709	Remote Similarity	NPD2950	Approved
0.6706	Remote Similarity	NPD7091	Discontinued
0.6705	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4783	Approved
0.6688	Remote Similarity	NPD4781	Approved
0.6687	Remote Similarity	NPD2365	Approved
0.6686	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6017	Discontinued
0.6667	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4549	Discontinued
0.6648	Remote Similarity	NPD8241	Phase 2
0.6647	Remote Similarity	NPD7072	Phase 2
0.6647	Remote Similarity	NPD4942	Approved
0.6646	Remote Similarity	NPD2129	Approved
0.6645	Remote Similarity	NPD1949	Approved
0.6645	Remote Similarity	NPD1950	Approved
0.6643	Remote Similarity	NPD1065	Approved
0.6643	Remote Similarity	NPD1064	Approved
0.6627	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2508	Discontinued
0.6622	Remote Similarity	NPD3867	Phase 2
0.66	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7786	Discontinued
0.6573	Remote Similarity	NPD7854	Phase 2
0.657	Remote Similarity	NPD8060	Phase 1
0.6566	Remote Similarity	NPD7295	Approved
0.6558	Remote Similarity	NPD6408	Phase 1
0.6556	Remote Similarity	NPD5600	Discontinued
0.6556	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7795	Phase 2
0.6554	Remote Similarity	NPD3387	Approved
0.655	Remote Similarity	NPD5741	Approved
0.655	Remote Similarity	NPD5742	Approved
0.655	Remote Similarity	NPD5743	Approved
0.6548	Remote Similarity	NPD4432	Discontinued
0.6545	Remote Similarity	NPD7082	Approved
0.6543	Remote Similarity	NPD6342	Discontinued
0.6534	Remote Similarity	NPD5678	Approved
0.6533	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1344	Phase 2
0.6531	Remote Similarity	NPD2124	Approved
0.6519	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7771	Discontinued
0.6519	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3790	Phase 2
0.6512	Remote Similarity	NPD1663	Discontinued
0.6506	Remote Similarity	NPD7259	Approved
0.65	Remote Similarity	NPD1527	Phase 2
0.65	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4120	Approved
0.6491	Remote Similarity	NPD4121	Phase 3
0.6489	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6639	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7093	Approved
0.6484	Remote Similarity	NPD6879	Phase 2
0.6484	Remote Similarity	NPD6878	Phase 2
0.6484	Remote Similarity	NPD7092	Approved
0.6481	Remote Similarity	NPD8125	Discontinued
0.6479	Remote Similarity	NPD4803	Discontinued
0.6478	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2962	Approved
0.6474	Remote Similarity	NPD2961	Approved
0.646	Remote Similarity	NPD5184	Approved
0.646	Remote Similarity	NPD5182	Approved
0.646	Remote Similarity	NPD5185	Approved
0.646	Remote Similarity	NPD7200	Approved
0.6458	Remote Similarity	NPD7308	Discontinued
0.6452	Remote Similarity	NPD7461	Approved
0.645	Remote Similarity	NPD979	Approved
0.6447	Remote Similarity	NPD5657	Phase 3
0.6444	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1175	Approved
0.6437	Remote Similarity	NPD6629	Discontinued
0.6436	Remote Similarity	NPD7434	Approved
0.6433	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6900	Discontinued
0.6429	Remote Similarity	NPD1123	Approved
0.6429	Remote Similarity	NPD1124	Approved
0.6429	Remote Similarity	NPD5775	Approved
0.6429	Remote Similarity	NPD5774	Approved
0.6425	Remote Similarity	NPD7663	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2093	Discontinued
0.6421	Remote Similarity	NPD7619	Phase 3
0.6421	Remote Similarity	NPD7618	Phase 3
0.6419	Remote Similarity	NPD2038	Approved
0.6419	Remote Similarity	NPD3865	Approved
0.6419	Remote Similarity	NPD2039	Approved
0.6415	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5748	Phase 2
0.6405	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5809	Phase 3
0.6398	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3581	Discontinued
0.6392	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7478	Approved
0.6391	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5997	Discontinued
0.6387	Remote Similarity	NPD4176	Approved
0.6387	Remote Similarity	NPD4178	Approved
0.6386	Remote Similarity	NPD6513	Approved
0.6386	Remote Similarity	NPD6512	Approved
0.638	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7483	Phase 2
0.6378	Remote Similarity	NPD7482	Phase 2
0.6374	Remote Similarity	NPD7606	Phase 3
0.6374	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5840	Discontinued
0.637	Remote Similarity	NPD4114	Approved
0.637	Remote Similarity	NPD5253	Approved
0.637	Remote Similarity	NPD4115	Approved
0.6369	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7210	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