NPASS Compound

Structure

NPC472119 OpenBabel07101719132D 22 26 0 0 1 0 0 0 0 0999 V2000 -4.0556 0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9133 2.9845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3650 1.1060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3650 1.8448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2748 0.7366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2748 2.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8137 0.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8464 1.6797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7918 -0.5399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9145 1.1060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6171 0.8777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2267 0.9486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5500 0.0464 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9145 1.8448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4929 -0.1247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7893 1.5085 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0513 1.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2688 0.9199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1126 0.6063 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6171 2.0730 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9038 2.4362 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 19 1 0 0 0 0 2 20 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 10 2 0 0 0 0 6 14 2 0 0 0 0 7 11 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 17 2 0 0 0 0 12 8 1 1 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 9 1 1 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 7 1 6 0 0 0 15 19 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.15
Volume:	303.494
LogP:	2.508
LogD:	2.148
LogS:	-2.688
# Rotatable Bonds:	0
TPSA:	34.47
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	4.63
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987
MDCK Permeability:	3.632243533502333e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.696
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.771
30% Bioavailability (F30%):	0.104

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	70.29612731933594%
Volume Distribution (VD):	2.618
Pgp-substrate:	39.142642974853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.686
CYP1A2-substrate:	0.491
CYP2C19-inhibitor:	0.204
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.733
CYP2D6-inhibitor:	0.712
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	10.543
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.55
AMES Toxicity:	0.305
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.128
Carcinogencity:	0.746
Eye Corrosion:	0.005
Eye Irritation:	0.06
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC472119

Natural Product ID:	NPC472119
*Common Name:**	KPCQTOKITJYXQO-VDERGJSUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KPCQTOKITJYXQO-VDERGJSUSA-N
Standard InCHI:	InChI=1S/C18H20N2O2/c1-19-15-7-11-10-5-3-4-6-14(10)20(2)17(11)16(19)8-12-13(15)9-22-18(12)21/h3-6,12-13,15-16H,7-9H2,1-2H3/t12-,13-,15+,16+/m1/s1
SMILES:	O=C1OC[C@@H]2[C@H]1C[C@@H]1N([C@H]2Cc2c1n(C)c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338242
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[501574]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[501574]

☑ 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 NPC472119 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	296
0.1-0.2	1401
0.2-0.3	8836
0.3-0.4	22452
0.4-0.5	4536
0.5-0.6	2574
0.6-0.7	2113
0.7-0.8	410
0.8-0.85	64
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9191	High Similarity	NPC472097
0.9128	High Similarity	NPC472323
0.9012	High Similarity	NPC472107
0.9012	High Similarity	NPC79062
0.9006	High Similarity	NPC143533
0.9	High Similarity	NPC15840
0.896	High Similarity	NPC66210
0.8953	High Similarity	NPC258480
0.8876	High Similarity	NPC245916
0.8678	High Similarity	NPC472104
0.867	High Similarity	NPC472098
0.8663	High Similarity	NPC234987
0.8644	High Similarity	NPC111602
0.8644	High Similarity	NPC63199
0.8644	High Similarity	NPC175474
0.8644	High Similarity	NPC196251
0.8644	High Similarity	NPC102338
0.8564	High Similarity	NPC472116
0.85	High Similarity	NPC472113
0.8492	Intermediate Similarity	NPC472112
0.847	Intermediate Similarity	NPC52557
0.8452	Intermediate Similarity	NPC81229
0.8452	Intermediate Similarity	NPC255229
0.8427	Intermediate Similarity	NPC478077
0.8409	Intermediate Similarity	NPC113626
0.8407	Intermediate Similarity	NPC289299
0.8407	Intermediate Similarity	NPC57994
0.8391	Intermediate Similarity	NPC24594
0.8391	Intermediate Similarity	NPC472122
0.8352	Intermediate Similarity	NPC469896
0.828	Intermediate Similarity	NPC312870
0.828	Intermediate Similarity	NPC254240
0.828	Intermediate Similarity	NPC49196
0.828	Intermediate Similarity	NPC313985
0.828	Intermediate Similarity	NPC79129
0.828	Intermediate Similarity	NPC249150
0.828	Intermediate Similarity	NPC195461
0.828	Intermediate Similarity	NPC128265
0.828	Intermediate Similarity	NPC294909
0.828	Intermediate Similarity	NPC199851
0.828	Intermediate Similarity	NPC81654
0.8249	Intermediate Similarity	NPC472105
0.8249	Intermediate Similarity	NPC187827
0.8207	Intermediate Similarity	NPC220151
0.8207	Intermediate Similarity	NPC19692
0.8187	Intermediate Similarity	NPC194881
0.8172	Intermediate Similarity	NPC50503
0.8158	Intermediate Similarity	NPC238457
0.8156	Intermediate Similarity	NPC472109
0.8156	Intermediate Similarity	NPC472110
0.814	Intermediate Similarity	NPC21174
0.814	Intermediate Similarity	NPC271797
0.8136	Intermediate Similarity	NPC326575
0.8095	Intermediate Similarity	NPC162730
0.809	Intermediate Similarity	NPC219336
0.809	Intermediate Similarity	NPC133261
0.8087	Intermediate Similarity	NPC314333
0.8087	Intermediate Similarity	NPC329858
0.8034	Intermediate Similarity	NPC15573
0.8034	Intermediate Similarity	NPC183662
0.8034	Intermediate Similarity	NPC217372
0.8	Intermediate Similarity	NPC55493
0.8	Intermediate Similarity	NPC474116
0.799	Intermediate Similarity	NPC472099
0.7989	Intermediate Similarity	NPC214428
0.7966	Intermediate Similarity	NPC161861
0.7966	Intermediate Similarity	NPC472123
0.7957	Intermediate Similarity	NPC81802
0.7957	Intermediate Similarity	NPC472295
0.7957	Intermediate Similarity	NPC269886
0.7957	Intermediate Similarity	NPC472210
0.7957	Intermediate Similarity	NPC247735
0.7956	Intermediate Similarity	NPC139291
0.7956	Intermediate Similarity	NPC472108
0.7908	Intermediate Similarity	NPC264176
0.7898	Intermediate Similarity	NPC317430
0.7876	Intermediate Similarity	NPC277350
0.7868	Intermediate Similarity	NPC234078
0.7868	Intermediate Similarity	NPC221100
0.7857	Intermediate Similarity	NPC159125
0.7835	Intermediate Similarity	NPC477065
0.7829	Intermediate Similarity	NPC469541
0.7826	Intermediate Similarity	NPC62749
0.7796	Intermediate Similarity	NPC469501
0.7796	Intermediate Similarity	NPC469470
0.779	Intermediate Similarity	NPC248462
0.7789	Intermediate Similarity	NPC148183
0.7789	Intermediate Similarity	NPC152768
0.7755	Intermediate Similarity	NPC469743
0.7744	Intermediate Similarity	NPC53344
0.774	Intermediate Similarity	NPC56233
0.7737	Intermediate Similarity	NPC469736
0.7735	Intermediate Similarity	NPC14113
0.7735	Intermediate Similarity	NPC145885
0.7735	Intermediate Similarity	NPC28848
0.7735	Intermediate Similarity	NPC14325
0.7735	Intermediate Similarity	NPC84827
0.7722	Intermediate Similarity	NPC469938
0.7718	Intermediate Similarity	NPC33949
0.7696	Intermediate Similarity	NPC149708
0.7688	Intermediate Similarity	NPC472291
0.766	Intermediate Similarity	NPC473763
0.766	Intermediate Similarity	NPC117244
0.7656	Intermediate Similarity	NPC241024
0.765	Intermediate Similarity	NPC91179
0.7637	Intermediate Similarity	NPC64436
0.763	Intermediate Similarity	NPC478076
0.7619	Intermediate Similarity	NPC472292
0.7611	Intermediate Similarity	NPC126492
0.7586	Intermediate Similarity	NPC52254
0.7582	Intermediate Similarity	NPC267885
0.7582	Intermediate Similarity	NPC84347
0.7576	Intermediate Similarity	NPC478158
0.7574	Intermediate Similarity	NPC20144
0.7565	Intermediate Similarity	NPC293917
0.7553	Intermediate Similarity	NPC321708
0.755	Intermediate Similarity	NPC475778
0.7541	Intermediate Similarity	NPC111275
0.754	Intermediate Similarity	NPC235684
0.7538	Intermediate Similarity	NPC234999
0.7537	Intermediate Similarity	NPC281049
0.7527	Intermediate Similarity	NPC110500
0.7527	Intermediate Similarity	NPC203468
0.7527	Intermediate Similarity	NPC149155
0.7513	Intermediate Similarity	NPC102008
0.7513	Intermediate Similarity	NPC67288
0.75	Intermediate Similarity	NPC126709
0.75	Intermediate Similarity	NPC248041
0.75	Intermediate Similarity	NPC78020
0.75	Intermediate Similarity	NPC472293
0.75	Intermediate Similarity	NPC104483
0.7488	Intermediate Similarity	NPC21638
0.7488	Intermediate Similarity	NPC305984
0.7486	Intermediate Similarity	NPC121903
0.7475	Intermediate Similarity	NPC478157
0.7474	Intermediate Similarity	NPC472296
0.7474	Intermediate Similarity	NPC472297
0.7462	Intermediate Similarity	NPC185742
0.7462	Intermediate Similarity	NPC475847
0.7451	Intermediate Similarity	NPC82070
0.7449	Intermediate Similarity	NPC57398
0.7449	Intermediate Similarity	NPC476874
0.7446	Intermediate Similarity	NPC211997
0.7438	Intermediate Similarity	NPC476114
0.7433	Intermediate Similarity	NPC472294
0.7432	Intermediate Similarity	NPC329688
0.7432	Intermediate Similarity	NPC189812
0.7426	Intermediate Similarity	NPC54744
0.7424	Intermediate Similarity	NPC472111
0.7419	Intermediate Similarity	NPC71037
0.7418	Intermediate Similarity	NPC158129
0.7405	Intermediate Similarity	NPC283219
0.7405	Intermediate Similarity	NPC55772
0.7405	Intermediate Similarity	NPC213468
0.7401	Intermediate Similarity	NPC129721
0.7401	Intermediate Similarity	NPC113946
0.7391	Intermediate Similarity	NPC134586
0.7385	Intermediate Similarity	NPC74413
0.7377	Intermediate Similarity	NPC476425
0.7376	Intermediate Similarity	NPC75634
0.7374	Intermediate Similarity	NPC473376
0.7374	Intermediate Similarity	NPC314648
0.7366	Intermediate Similarity	NPC174788
0.736	Intermediate Similarity	NPC260900
0.736	Intermediate Similarity	NPC137589
0.7358	Intermediate Similarity	NPC474121
0.7356	Intermediate Similarity	NPC475271
0.7354	Intermediate Similarity	NPC311858
0.7354	Intermediate Similarity	NPC315555
0.7353	Intermediate Similarity	NPC469928
0.7344	Intermediate Similarity	NPC471386
0.734	Intermediate Similarity	NPC229348
0.7337	Intermediate Similarity	NPC474145
0.7337	Intermediate Similarity	NPC475841
0.7333	Intermediate Similarity	NPC475258
0.733	Intermediate Similarity	NPC200743
0.7323	Intermediate Similarity	NPC476098
0.7316	Intermediate Similarity	NPC17059
0.7314	Intermediate Similarity	NPC40070
0.7313	Intermediate Similarity	NPC472070
0.7313	Intermediate Similarity	NPC469589
0.7306	Intermediate Similarity	NPC88315
0.7306	Intermediate Similarity	NPC192306
0.7304	Intermediate Similarity	NPC474412
0.7302	Intermediate Similarity	NPC62510
0.73	Intermediate Similarity	NPC314297
0.73	Intermediate Similarity	NPC315545
0.7296	Intermediate Similarity	NPC81535
0.7294	Intermediate Similarity	NPC88097
0.7291	Intermediate Similarity	NPC318299
0.7291	Intermediate Similarity	NPC118940
0.7288	Intermediate Similarity	NPC161827
0.7287	Intermediate Similarity	NPC19679
0.7287	Intermediate Similarity	NPC470205
0.7286	Intermediate Similarity	NPC909
0.7286	Intermediate Similarity	NPC475338
0.7282	Intermediate Similarity	NPC227582
0.7282	Intermediate Similarity	NPC96321
0.7277	Intermediate Similarity	NPC213629
0.7273	Intermediate Similarity	NPC193761

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 NPC472119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	485
0.2-0.3	661
0.3-0.4	1682
0.4-0.5	2530
0.5-0.6	2554
0.6-0.7	924
0.7-0.8	125
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8407	Intermediate Similarity	NPD4602	Approved
0.8324	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD4501	Approved
0.828	Intermediate Similarity	NPD4600	Approved
0.828	Intermediate Similarity	NPD4601	Approved
0.828	Intermediate Similarity	NPD4500	Approved
0.8191	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD4499	Approved
0.8075	Intermediate Similarity	NPD4397	Phase 1
0.7865	Intermediate Similarity	NPD750	Phase 2
0.7846	Intermediate Similarity	NPD4520	Approved
0.7795	Intermediate Similarity	NPD7666	Phase 3
0.7795	Intermediate Similarity	NPD7665	Phase 2
0.7778	Intermediate Similarity	NPD5104	Approved
0.7778	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD6999	Discontinued
0.7684	Intermediate Similarity	NPD2915	Discontinued
0.7663	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD5426	Phase 3
0.7622	Intermediate Similarity	NPD2096	Phase 2
0.7622	Intermediate Similarity	NPD2091	Phase 2
0.7609	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7001	Phase 3
0.7568	Intermediate Similarity	NPD2095	Phase 2
0.7568	Intermediate Similarity	NPD2094	Phase 2
0.7568	Intermediate Similarity	NPD2092	Phase 2
0.7568	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7234	Approved
0.7553	Intermediate Similarity	NPD7233	Approved
0.7539	Intermediate Similarity	NPD7944	Discontinued
0.7527	Intermediate Similarity	NPD482	Approved
0.7525	Intermediate Similarity	NPD2509	Approved
0.7525	Intermediate Similarity	NPD2510	Approved
0.7513	Intermediate Similarity	NPD7777	Approved
0.7513	Intermediate Similarity	NPD7778	Approved
0.7513	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD53	Approved
0.75	Intermediate Similarity	NPD4326	Phase 2
0.75	Intermediate Similarity	NPD2844	Phase 3
0.7487	Intermediate Similarity	NPD5075	Discontinued
0.7486	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD5003	Discontinued
0.746	Intermediate Similarity	NPD4334	Discontinued
0.7459	Intermediate Similarity	NPD5898	Approved
0.7459	Intermediate Similarity	NPD1573	Approved
0.7459	Intermediate Similarity	NPD5897	Approved
0.7459	Intermediate Similarity	NPD1575	Approved
0.7459	Intermediate Similarity	NPD5899	Approved
0.7448	Intermediate Similarity	NPD4427	Phase 2
0.7438	Intermediate Similarity	NPD3393	Approved
0.7438	Intermediate Similarity	NPD3394	Approved
0.7438	Intermediate Similarity	NPD3389	Approved
0.741	Intermediate Similarity	NPD3385	Approved
0.7398	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD5444	Phase 1
0.734	Intermediate Similarity	NPD7483	Phase 2
0.734	Intermediate Similarity	NPD7482	Phase 2
0.734	Intermediate Similarity	NPD6178	Phase 3
0.7337	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7470	Discontinued
0.7323	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5472	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4948	Discontinued
0.7293	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4918	Discontinued
0.7291	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6987	Phase 1
0.7277	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1630	Approved
0.7254	Intermediate Similarity	NPD4315	Phase 2
0.7254	Intermediate Similarity	NPD5505	Discontinued
0.7253	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD2565	Phase 2
0.724	Intermediate Similarity	NPD2564	Approved
0.7228	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5293	Phase 2
0.7204	Intermediate Similarity	NPD5471	Phase 3
0.7202	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7103	Approved
0.7181	Intermediate Similarity	NPD6452	Discontinued
0.7178	Intermediate Similarity	NPD2916	Discontinued
0.7175	Intermediate Similarity	NPD2882	Phase 1
0.7172	Intermediate Similarity	NPD6479	Discontinued
0.7169	Intermediate Similarity	NPD3654	Approved
0.7164	Intermediate Similarity	NPD7957	Phase 1
0.7164	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8072	Approved
0.715	Intermediate Similarity	NPD7688	Phase 1
0.7143	Intermediate Similarity	NPD1631	Approved
0.7143	Intermediate Similarity	NPD1683	Approved
0.7143	Intermediate Similarity	NPD6995	Phase 1
0.7121	Intermediate Similarity	NPD6249	Phase 2
0.7121	Intermediate Similarity	NPD6248	Phase 2
0.712	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6227	Discontinued
0.712	Intermediate Similarity	NPD4639	Approved
0.712	Intermediate Similarity	NPD4640	Approved
0.712	Intermediate Similarity	NPD4638	Approved
0.7116	Intermediate Similarity	NPD4885	Approved
0.7114	Intermediate Similarity	NPD3947	Discontinued
0.7114	Intermediate Similarity	NPD5901	Discontinued
0.7113	Intermediate Similarity	NPD2336	Approved
0.711	Intermediate Similarity	NPD5020	Approved
0.7107	Intermediate Similarity	NPD6206	Phase 1
0.7102	Intermediate Similarity	NPD4547	Phase 3
0.7098	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5891	Approved
0.7092	Intermediate Similarity	NPD4418	Discontinued
0.7089	Intermediate Similarity	NPD7730	Approved
0.7089	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7731	Approved
0.7083	Intermediate Similarity	NPD7952	Approved
0.7083	Intermediate Similarity	NPD7950	Approved
0.7083	Intermediate Similarity	NPD7789	Approved
0.7083	Intermediate Similarity	NPD7791	Approved
0.7083	Intermediate Similarity	NPD7953	Approved
0.7083	Intermediate Similarity	NPD7951	Approved
0.7083	Intermediate Similarity	NPD7790	Approved
0.7083	Intermediate Similarity	NPD5809	Phase 3
0.7079	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6158	Phase 2
0.7079	Intermediate Similarity	NPD7568	Phase 1
0.7075	Intermediate Similarity	NPD7271	Approved
0.7071	Intermediate Similarity	NPD6261	Phase 3
0.7071	Intermediate Similarity	NPD6846	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8326	Phase 3
0.7067	Intermediate Similarity	NPD8325	Phase 3
0.7065	Intermediate Similarity	NPD6176	Phase 1
0.7065	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6281	Approved
0.7056	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4204	Approved
0.7053	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4203	Approved
0.7044	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2896	Discontinued
0.7033	Intermediate Similarity	NPD2511	Approved
0.7031	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8114	Approved
0.703	Intermediate Similarity	NPD8115	Approved
0.7027	Intermediate Similarity	NPD5862	Discovery
0.7023	Intermediate Similarity	NPD4952	Phase 3
0.7023	Intermediate Similarity	NPD7824	Approved
0.702	Intermediate Similarity	NPD2880	Discontinued
0.7011	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD43	Approved
0.7005	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6182	Approved
0.7	Intermediate Similarity	NPD6770	Approved
0.7	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6595	Phase 3
0.7	Intermediate Similarity	NPD5473	Discontinued
0.6994	Remote Similarity	NPD4804	Approved
0.699	Remote Similarity	NPD6665	Discontinued
0.6989	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2144	Approved
0.6979	Remote Similarity	NPD4957	Phase 2
0.6977	Remote Similarity	NPD6554	Approved
0.6977	Remote Similarity	NPD45	Approved
0.6976	Remote Similarity	NPD4506	Discontinued
0.6971	Remote Similarity	NPD4897	Phase 2
0.6971	Remote Similarity	NPD4047	Discontinued
0.697	Remote Similarity	NPD2307	Discontinued
0.6968	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1586	Approved
0.6963	Remote Similarity	NPD3038	Discontinued
0.6957	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4852	Phase 2
0.6952	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5555	Phase 1
0.6942	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6733	Discontinued
0.6935	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD8073	Approved
0.6927	Remote Similarity	NPD4373	Phase 2
0.6927	Remote Similarity	NPD8399	Phase 1

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