NPASS Compound

Structure

NPC470877 OpenBabel07101719512D 21 21 0 0 0 0 0 0 0 0999 V2000 -6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 19 20 2 3 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.24
Volume:	337.865
LogP:	5.819
LogD:	4.258
LogS:	-4.501
# Rotatable Bonds:	13
TPSA:	29.1
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	1.588
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.629
MDCK Permeability:	1.4899936104484368e-05
Pgp-inhibitor:	0.065
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.612
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	97.35662078857422%
Volume Distribution (VD):	1.293
Pgp-substrate:	1.133385181427002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.556
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.791
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.451
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.492
CYP2D6-substrate:	0.367
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	6.034
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.528
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.912
Carcinogencity:	0.031
Eye Corrosion:	0.011
Eye Irritation:	0.252
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC470877

Natural Product ID:	NPC470877
*Common Name:**	N-Benzyldodecanamide
IUPAC Name:	N-benzyldodecanamide
Synonyms:
Standard InCHIKey:	AAJQYMJRUXQQCP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H31NO/c1-2-3-4-5-6-7-8-9-13-16-19(21)20-17-18-14-11-10-12-15-18/h10-12,14-15H,2-9,13,16-17H2,1H3,(H,20,21)
SMILES:	CCCCCCCCCCCC(=O)NCC1=CC=CC=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2273099
PubChem CID:	54134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

*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
NPO32564	Echinacea	Genus	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26105195]

☑ 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	3
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4515	Individual Protein	NADH-ubiquinone oxidoreductase chain 1	Bos taurus	IC50	=	21877.62	nM	PMID[572937]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	32.4	%	PMID[572938]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[572937]
NPT2	Others	Unspecified		IC50	=	12022.64	nM	PMID[572937]

☑ 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 NPC470877 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	98
0.1-0.2	1667
0.2-0.3	9303
0.3-0.4	17915
0.4-0.5	10291
0.5-0.6	2735
0.6-0.7	532
0.7-0.8	121
0.8-0.85	8
0.85-0.9	14
0.9-0.95	0
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC121872
0.9881	High Similarity	NPC78041
0.9881	High Similarity	NPC471307
0.9881	High Similarity	NPC141139
0.9881	High Similarity	NPC74936
0.9881	High Similarity	NPC209764
0.9881	High Similarity	NPC159178
0.954	High Similarity	NPC471309
0.8851	High Similarity	NPC473031
0.8791	High Similarity	NPC58674
0.875	High Similarity	NPC12429
0.8737	High Similarity	NPC471310
0.8737	High Similarity	NPC471317
0.8696	High Similarity	NPC25565
0.8636	High Similarity	NPC471638
0.8602	High Similarity	NPC475439
0.8602	High Similarity	NPC473501
0.8587	High Similarity	NPC161972
0.8587	High Similarity	NPC303045
0.8556	High Similarity	NPC316108
0.8556	High Similarity	NPC172128
0.8542	High Similarity	NPC202613
0.8462	Intermediate Similarity	NPC226438
0.8404	Intermediate Similarity	NPC311242
0.8261	Intermediate Similarity	NPC245259
0.8132	Intermediate Similarity	NPC325441
0.8111	Intermediate Similarity	NPC203076
0.8081	Intermediate Similarity	NPC224610
0.8081	Intermediate Similarity	NPC113326
0.8081	Intermediate Similarity	NPC88267
0.8081	Intermediate Similarity	NPC194390
0.8068	Intermediate Similarity	NPC14326
0.8046	Intermediate Similarity	NPC192623
0.7957	Intermediate Similarity	NPC258627
0.7857	Intermediate Similarity	NPC12730
0.7835	Intermediate Similarity	NPC33168
0.783	Intermediate Similarity	NPC471318
0.7826	Intermediate Similarity	NPC198747
0.7802	Intermediate Similarity	NPC3210
0.7745	Intermediate Similarity	NPC231705
0.7745	Intermediate Similarity	NPC327481
0.7692	Intermediate Similarity	NPC258056
0.7647	Intermediate Similarity	NPC211551
0.7624	Intermediate Similarity	NPC178681
0.7619	Intermediate Similarity	NPC474149
0.76	Intermediate Similarity	NPC469457
0.7586	Intermediate Similarity	NPC271642
0.7579	Intermediate Similarity	NPC78154
0.7558	Intermediate Similarity	NPC299134
0.7551	Intermediate Similarity	NPC471320
0.7551	Intermediate Similarity	NPC471319
0.7526	Intermediate Similarity	NPC476483
0.75	Intermediate Similarity	NPC142297
0.7477	Intermediate Similarity	NPC474584
0.7471	Intermediate Similarity	NPC98976
0.7453	Intermediate Similarity	NPC319579
0.7451	Intermediate Similarity	NPC178902
0.7451	Intermediate Similarity	NPC164859
0.7442	Intermediate Similarity	NPC244738
0.7423	Intermediate Similarity	NPC265521
0.7411	Intermediate Similarity	NPC53596
0.7411	Intermediate Similarity	NPC289330
0.7411	Intermediate Similarity	NPC160120
0.7411	Intermediate Similarity	NPC17388
0.7411	Intermediate Similarity	NPC471308
0.7407	Intermediate Similarity	NPC276949
0.7407	Intermediate Similarity	NPC35850
0.7339	Intermediate Similarity	NPC33742
0.7326	Intermediate Similarity	NPC208302
0.7303	Intermediate Similarity	NPC98269
0.7303	Intermediate Similarity	NPC325662
0.7273	Intermediate Similarity	NPC317254
0.7273	Intermediate Similarity	NPC189371
0.7264	Intermediate Similarity	NPC96224
0.7264	Intermediate Similarity	NPC24101
0.7255	Intermediate Similarity	NPC214200
0.7255	Intermediate Similarity	NPC228400
0.7238	Intermediate Similarity	NPC191215
0.7238	Intermediate Similarity	NPC274089
0.7222	Intermediate Similarity	NPC329011
0.7222	Intermediate Similarity	NPC12857
0.7217	Intermediate Similarity	NPC471315
0.7217	Intermediate Similarity	NPC471314
0.7209	Intermediate Similarity	NPC219246
0.7207	Intermediate Similarity	NPC470544
0.7204	Intermediate Similarity	NPC15839
0.72	Intermediate Similarity	NPC3371
0.7184	Intermediate Similarity	NPC318154
0.7182	Intermediate Similarity	NPC118202
0.7159	Intermediate Similarity	NPC108218
0.7143	Intermediate Similarity	NPC169328
0.7143	Intermediate Similarity	NPC254088
0.7143	Intermediate Similarity	NPC470545
0.7117	Intermediate Similarity	NPC197470
0.7117	Intermediate Similarity	NPC188010
0.7103	Intermediate Similarity	NPC153690
0.71	Intermediate Similarity	NPC215351
0.71	Intermediate Similarity	NPC108339
0.71	Intermediate Similarity	NPC20142
0.708	Intermediate Similarity	NPC310467
0.708	Intermediate Similarity	NPC237420
0.708	Intermediate Similarity	NPC470546
0.708	Intermediate Similarity	NPC314992
0.7075	Intermediate Similarity	NPC130898
0.7075	Intermediate Similarity	NPC474973
0.7075	Intermediate Similarity	NPC474804
0.7071	Intermediate Similarity	NPC323164
0.7065	Intermediate Similarity	NPC164449
0.7065	Intermediate Similarity	NPC184030
0.7065	Intermediate Similarity	NPC309279
0.7059	Intermediate Similarity	NPC226096
0.7059	Intermediate Similarity	NPC108606
0.7059	Intermediate Similarity	NPC164514
0.7059	Intermediate Similarity	NPC290515
0.7059	Intermediate Similarity	NPC303611
0.7054	Intermediate Similarity	NPC2265
0.7054	Intermediate Similarity	NPC82963
0.7033	Intermediate Similarity	NPC224544
0.7027	Intermediate Similarity	NPC470550
0.7027	Intermediate Similarity	NPC205652
0.7021	Intermediate Similarity	NPC104070
0.7021	Intermediate Similarity	NPC477770
0.7021	Intermediate Similarity	NPC146703
0.7019	Intermediate Similarity	NPC327226
0.7018	Intermediate Similarity	NPC283760
0.7011	Intermediate Similarity	NPC229235
0.7	Intermediate Similarity	NPC139658
0.6991	Remote Similarity	NPC38458
0.6991	Remote Similarity	NPC311737
0.6989	Remote Similarity	NPC307456
0.6981	Remote Similarity	NPC143516
0.6966	Remote Similarity	NPC122327
0.6966	Remote Similarity	NPC113000
0.6966	Remote Similarity	NPC112609
0.6961	Remote Similarity	NPC122493
0.6961	Remote Similarity	NPC10781
0.6961	Remote Similarity	NPC293628
0.6957	Remote Similarity	NPC45777
0.6957	Remote Similarity	NPC478014
0.6957	Remote Similarity	NPC478015
0.6957	Remote Similarity	NPC478016
0.6957	Remote Similarity	NPC477061
0.6957	Remote Similarity	NPC476990
0.6947	Remote Similarity	NPC169016
0.6937	Remote Similarity	NPC474544
0.6937	Remote Similarity	NPC1986
0.6923	Remote Similarity	NPC155847
0.6923	Remote Similarity	NPC289381
0.6915	Remote Similarity	NPC475199
0.6915	Remote Similarity	NPC283012
0.6915	Remote Similarity	NPC121478
0.6915	Remote Similarity	NPC73637
0.6903	Remote Similarity	NPC147957
0.6897	Remote Similarity	NPC202521
0.6897	Remote Similarity	NPC71684
0.6893	Remote Similarity	NPC322598
0.6889	Remote Similarity	NPC276699
0.6887	Remote Similarity	NPC150254
0.6887	Remote Similarity	NPC226778
0.6887	Remote Similarity	NPC147000
0.6887	Remote Similarity	NPC304761
0.6875	Remote Similarity	NPC142599
0.687	Remote Similarity	NPC43275
0.687	Remote Similarity	NPC268572
0.6842	Remote Similarity	NPC119677
0.6842	Remote Similarity	NPC44830
0.6842	Remote Similarity	NPC474088
0.6838	Remote Similarity	NPC252878
0.6822	Remote Similarity	NPC67043
0.6822	Remote Similarity	NPC476198
0.6814	Remote Similarity	NPC235421
0.681	Remote Similarity	NPC190663
0.681	Remote Similarity	NPC80150
0.6809	Remote Similarity	NPC133050
0.6809	Remote Similarity	NPC231986
0.68	Remote Similarity	NPC470926
0.6796	Remote Similarity	NPC324569
0.678	Remote Similarity	NPC46427
0.678	Remote Similarity	NPC35996
0.678	Remote Similarity	NPC6975
0.6771	Remote Similarity	NPC304538
0.6762	Remote Similarity	NPC29601
0.6759	Remote Similarity	NPC45033
0.6754	Remote Similarity	NPC239357
0.6742	Remote Similarity	NPC121708
0.6742	Remote Similarity	NPC125144
0.6739	Remote Similarity	NPC290638
0.6737	Remote Similarity	NPC99394
0.6737	Remote Similarity	NPC103326
0.6737	Remote Similarity	NPC87299
0.6737	Remote Similarity	NPC329319
0.6733	Remote Similarity	NPC473661
0.6731	Remote Similarity	NPC107619
0.6729	Remote Similarity	NPC275467
0.6727	Remote Similarity	NPC292758
0.6727	Remote Similarity	NPC65855
0.6723	Remote Similarity	NPC22746
0.6702	Remote Similarity	NPC127343
0.6701	Remote Similarity	NPC474354
0.6701	Remote Similarity	NPC99482

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 NPC470877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	618
0.2-0.3	1042
0.3-0.4	2346
0.4-0.5	3037
0.5-0.6	1534
0.6-0.7	394
0.7-0.8	79
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9651	High Similarity	NPD6690	Approved
0.8571	High Similarity	NPD1814	Approved
0.8571	High Similarity	NPD1812	Approved
0.8427	Intermediate Similarity	NPD187	Approved
0.8333	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1080	Approved
0.8191	Intermediate Similarity	NPD4814	Discontinued
0.8105	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD3066	Phase 2
0.7981	Intermediate Similarity	NPD4165	Phase 2
0.7826	Intermediate Similarity	NPD9538	Approved
0.7742	Intermediate Similarity	NPD1101	Approved
0.77	Intermediate Similarity	NPD4119	Approved
0.7684	Intermediate Similarity	NPD530	Approved
0.767	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5371	Approved
0.764	Intermediate Similarity	NPD5372	Approved
0.7629	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD1542	Approved
0.7619	Intermediate Similarity	NPD3644	Approved
0.7619	Intermediate Similarity	NPD3642	Approved
0.7619	Intermediate Similarity	NPD3643	Approved
0.7604	Intermediate Similarity	NPD752	Approved
0.7596	Intermediate Similarity	NPD2678	Approved
0.7596	Intermediate Similarity	NPD2679	Approved
0.757	Intermediate Similarity	NPD2658	Approved
0.757	Intermediate Similarity	NPD3150	Approved
0.757	Intermediate Similarity	NPD3148	Approved
0.757	Intermediate Similarity	NPD3149	Approved
0.757	Intermediate Similarity	NPD2659	Approved
0.757	Intermediate Similarity	NPD3147	Approved
0.7551	Intermediate Similarity	NPD2895	Discontinued
0.7549	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1394	Approved
0.7525	Intermediate Similarity	NPD1540	Approved
0.75	Intermediate Similarity	NPD1067	Discontinued
0.75	Intermediate Similarity	NPD603	Approved
0.7477	Intermediate Similarity	NPD1762	Approved
0.7477	Intermediate Similarity	NPD2212	Approved
0.7477	Intermediate Similarity	NPD2210	Approved
0.7477	Intermediate Similarity	NPD1764	Approved
0.7476	Intermediate Similarity	NPD5717	Approved
0.7476	Intermediate Similarity	NPD563	Approved
0.7476	Intermediate Similarity	NPD564	Approved
0.7451	Intermediate Similarity	NPD2244	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5103	Approved
0.7442	Intermediate Similarity	NPD9728	Phase 1
0.7431	Intermediate Similarity	NPD2622	Approved
0.74	Intermediate Similarity	NPD4117	Approved
0.7379	Intermediate Similarity	NPD3407	Phase 3
0.7353	Intermediate Similarity	NPD1417	Approved
0.7353	Intermediate Similarity	NPD1419	Approved
0.7347	Intermediate Similarity	NPD720	Approved
0.7347	Intermediate Similarity	NPD1409	Phase 3
0.7347	Intermediate Similarity	NPD1066	Discontinued
0.7347	Intermediate Similarity	NPD719	Approved
0.7333	Intermediate Similarity	NPD6406	Approved
0.7312	Intermediate Similarity	NPD2538	Approved
0.7312	Intermediate Similarity	NPD2539	Approved
0.7308	Intermediate Similarity	NPD999	Phase 2
0.7308	Intermediate Similarity	NPD1018	Approved
0.7196	Intermediate Similarity	NPD1107	Approved
0.7196	Intermediate Similarity	NPD1108	Approved
0.7184	Intermediate Similarity	NPD854	Approved
0.7184	Intermediate Similarity	NPD855	Approved
0.7184	Intermediate Similarity	NPD5716	Approved
0.7184	Intermediate Similarity	NPD4818	Approved
0.7184	Intermediate Similarity	NPD4719	Phase 2
0.7184	Intermediate Similarity	NPD4817	Approved
0.7174	Intermediate Similarity	NPD472	Approved
0.7172	Intermediate Similarity	NPD3718	Approved
0.7172	Intermediate Similarity	NPD3719	Approved
0.717	Intermediate Similarity	NPD2243	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD181	Approved
0.7143	Intermediate Similarity	NPD508	Approved
0.7143	Intermediate Similarity	NPD507	Approved
0.7143	Intermediate Similarity	NPD6360	Discontinued
0.7143	Intermediate Similarity	NPD1040	Phase 2
0.7129	Intermediate Similarity	NPD1875	Phase 1
0.7117	Intermediate Similarity	NPD1348	Approved
0.7111	Intermediate Similarity	NPD4147	Approved
0.7111	Intermediate Similarity	NPD4144	Approved
0.7094	Intermediate Similarity	NPD6325	Discontinued
0.7091	Intermediate Similarity	NPD1682	Approved
0.7091	Intermediate Similarity	NPD1680	Approved
0.7091	Intermediate Similarity	NPD1681	Approved
0.708	Intermediate Similarity	NPD2217	Approved
0.708	Intermediate Similarity	NPD2218	Phase 2
0.7064	Intermediate Similarity	NPD3651	Discontinued
0.7059	Intermediate Similarity	NPD9611	Approved
0.7059	Intermediate Similarity	NPD9612	Approved
0.7059	Intermediate Similarity	NPD9609	Approved
0.7018	Intermediate Similarity	NPD5981	Approved
0.6991	Remote Similarity	NPD7522	Discontinued
0.699	Remote Similarity	NPD9712	Approved
0.6966	Remote Similarity	NPD9594	Approved
0.6966	Remote Similarity	NPD80	Approved
0.6966	Remote Similarity	NPD9591	Approved
0.6966	Remote Similarity	NPD9589	Approved
0.6966	Remote Similarity	NPD9592	Approved
0.6966	Remote Similarity	NPD9588	Approved
0.6966	Remote Similarity	NPD9590	Approved
0.6966	Remote Similarity	NPD9593	Approved
0.6961	Remote Similarity	NPD9566	Approved
0.6957	Remote Similarity	NPD1052	Approved
0.6957	Remote Similarity	NPD1053	Approved
0.6957	Remote Similarity	NPD1051	Approved
0.6957	Remote Similarity	NPD7342	Discontinued
0.6952	Remote Similarity	NPD4656	Approved
0.6952	Remote Similarity	NPD4231	Approved
0.6952	Remote Similarity	NPD4229	Approved
0.6952	Remote Similarity	NPD3682	Approved
0.6952	Remote Similarity	NPD3680	Approved
0.6952	Remote Similarity	NPD4658	Approved
0.6952	Remote Similarity	NPD3683	Approved
0.6952	Remote Similarity	NPD1415	Approved
0.6952	Remote Similarity	NPD3681	Approved
0.6949	Remote Similarity	NPD5578	Approved
0.6949	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7156	Discontinued
0.6939	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD23	Approved
0.6931	Remote Similarity	NPD3772	Phase 3
0.6917	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.69	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD9710	Approved
0.6893	Remote Similarity	NPD9711	Approved
0.6893	Remote Similarity	NPD253	Approved
0.6891	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD310	Approved
0.6887	Remote Similarity	NPD10	Approved
0.6887	Remote Similarity	NPD314	Approved
0.6887	Remote Similarity	NPD309	Approved
0.6887	Remote Similarity	NPD315	Approved
0.6887	Remote Similarity	NPD311	Approved
0.6875	Remote Similarity	NPD5631	Phase 3
0.687	Remote Similarity	NPD1922	Discontinued
0.687	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD9722	Approved
0.6857	Remote Similarity	NPD9721	Approved
0.6852	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD295	Approved
0.6848	Remote Similarity	NPD293	Approved
0.6848	Remote Similarity	NPD296	Approved
0.6818	Remote Similarity	NPD4254	Approved
0.6818	Remote Similarity	NPD4253	Approved
0.6818	Remote Similarity	NPD2583	Phase 2
0.6814	Remote Similarity	NPD4031	Approved
0.6814	Remote Similarity	NPD4032	Approved
0.6814	Remote Similarity	NPD7508	Discontinued
0.6809	Remote Similarity	NPD3035	Approved
0.6809	Remote Similarity	NPD4026	Approved
0.6809	Remote Similarity	NPD4027	Approved
0.6803	Remote Similarity	NPD4738	Phase 2
0.68	Remote Similarity	NPD517	Discontinued
0.68	Remote Similarity	NPD3000	Approved
0.68	Remote Similarity	NPD2998	Approved
0.68	Remote Similarity	NPD2997	Approved
0.6796	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6093	Discontinued
0.678	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD590	Approved
0.6774	Remote Similarity	NPD589	Approved
0.6771	Remote Similarity	NPD5178	Approved
0.6771	Remote Similarity	NPD9395	Approved
0.6768	Remote Similarity	NPD9	Approved
0.6768	Remote Similarity	NPD297	Approved
0.6765	Remote Similarity	NPD7343	Discovery
0.6765	Remote Similarity	NPD7344	Phase 1
0.6759	Remote Similarity	NPD1445	Approved
0.6759	Remote Similarity	NPD1444	Approved
0.6754	Remote Similarity	NPD5162	Approved
0.6754	Remote Similarity	NPD3123	Discovery
0.6754	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD292	Approved
0.6742	Remote Similarity	NPD294	Approved
0.6737	Remote Similarity	NPD4169	Approved
0.6737	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4170	Approved
0.6733	Remote Similarity	NPD4405	Approved
0.6733	Remote Similarity	NPD4407	Approved
0.6733	Remote Similarity	NPD4408	Approved
0.6731	Remote Similarity	NPD1724	Approved
0.6729	Remote Similarity	NPD9608	Approved
0.6729	Remote Similarity	NPD9610	Approved
0.6723	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1736	Approved
0.6698	Remote Similarity	NPD1735	Approved
0.6698	Remote Similarity	NPD1737	Approved
0.6696	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7121	Approved
0.6694	Remote Similarity	NPD8118	Discontinued
0.6694	Remote Similarity	NPD7477	Discontinued
0.6694	Remote Similarity	NPD2674	Phase 3

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