NPASS Compound

Structure

NPC469554 OpenBabel07101718332D 35 40 0 0 1 0 0 0 0 0999 V2000 2.1857 -5.0143 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0269 -4.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0214 -4.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1693 -4.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 -3.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5760 -3.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -3.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1748 -4.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9882 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 -3.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9937 -3.0827 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 4.3301 -1.5000 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 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 -2.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5925 -4.1007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 29 1 0 0 0 0 15 23 1 0 0 0 0 15 30 2 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 26 2 0 0 0 0 18 24 1 0 0 0 0 18 25 2 0 0 0 0 19 31 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 22 34 1 0 0 0 0 23 24 2 0 0 0 0 23 35 1 0 0 0 0 24 27 1 0 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 31 1 0 0 0 0 27 32 1 0 0 0 0 28 29 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.2
Volume:	480.226
LogP:	4.708
LogD:	3.507
LogS:	-4.736
# Rotatable Bonds:	7
TPSA:	85.05
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	3.472
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.219
MDCK Permeability:	8.50697688292712e-06
Pgp-inhibitor:	0.846
Pgp-substrate:	0.897
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.232

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	96.03131103515625%
Volume Distribution (VD):	1.116
Pgp-substrate:	4.148112773895264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.824
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.686
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	4.025
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.621
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.786
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.484
Carcinogencity:	0.432
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.993

Download Data

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

Natural Product: NPC469554

Natural Product ID:	NPC469554
*Common Name:**	Quassidine D
IUPAC Name:	4,8-dimethoxy-1-[3-methoxy-3-(9H-pyrido[3,4-b]indol-1-yl)propyl]-9H-pyrido[3,4-b]indole
Synonyms:	Quassidine D
Standard InCHIKey:	PWYKKQVFQMAMNL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H26N4O3/c1-33-21-10-6-8-18-24-23(35-3)15-30-20(27(24)32-25(18)21)11-12-22(34-2)28-26-17(13-14-29-28)16-7-4-5-9-19(16)31-26/h4-10,13-15,22,31-32H,11-12H2,1-3H3
SMILES:	COC1=CC=CC2=C1NC3=C2C(=CN=C3CCC(C4=NC=CC5=C4NC6=CC=CC=C56)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087137
PubChem CID:	46184323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala 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
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[532629]

☑ 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 NPC469554 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	725
0.1-0.2	4152
0.2-0.3	13117
0.3-0.4	13476
0.4-0.5	6517
0.5-0.6	2573
0.6-0.7	1694
0.7-0.8	402
0.8-0.85	23
0.85-0.9	9
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC101543
0.9198	High Similarity	NPC314954
0.9171	High Similarity	NPC26679
0.9024	High Similarity	NPC185782
0.8913	High Similarity	NPC152620
0.8899	High Similarity	NPC53534
0.878	High Similarity	NPC476138
0.878	High Similarity	NPC245816
0.8768	High Similarity	NPC470799
0.8768	High Similarity	NPC8022
0.8761	High Similarity	NPC26543
0.8708	High Similarity	NPC167860
0.8708	High Similarity	NPC123976
0.8634	High Similarity	NPC19872
0.8558	High Similarity	NPC213530
0.8558	High Similarity	NPC193267
0.8454	Intermediate Similarity	NPC176538
0.8451	Intermediate Similarity	NPC94157
0.8411	Intermediate Similarity	NPC476287
0.8357	Intermediate Similarity	NPC5145
0.8333	Intermediate Similarity	NPC475774
0.8325	Intermediate Similarity	NPC232727
0.8294	Intermediate Similarity	NPC285558
0.8265	Intermediate Similarity	NPC132642
0.8227	Intermediate Similarity	NPC310118
0.8221	Intermediate Similarity	NPC267928
0.8211	Intermediate Similarity	NPC476041
0.8211	Intermediate Similarity	NPC304926
0.8136	Intermediate Similarity	NPC292958
0.8125	Intermediate Similarity	NPC110151
0.8125	Intermediate Similarity	NPC473185
0.8122	Intermediate Similarity	NPC470500
0.8112	Intermediate Similarity	NPC471891
0.8106	Intermediate Similarity	NPC180504
0.8091	Intermediate Similarity	NPC469594
0.8082	Intermediate Similarity	NPC170114
0.8073	Intermediate Similarity	NPC469592
0.8073	Intermediate Similarity	NPC471080
0.8065	Intermediate Similarity	NPC208284
0.8057	Intermediate Similarity	NPC476167
0.8052	Intermediate Similarity	NPC148889
0.8037	Intermediate Similarity	NPC470549
0.8035	Intermediate Similarity	NPC295228
0.8018	Intermediate Similarity	NPC199667
0.8018	Intermediate Similarity	NPC475253
0.8018	Intermediate Similarity	NPC476451
0.8009	Intermediate Similarity	NPC192315
0.8009	Intermediate Similarity	NPC477861
0.7991	Intermediate Similarity	NPC223427
0.799	Intermediate Similarity	NPC84853
0.7974	Intermediate Similarity	NPC81175
0.7973	Intermediate Similarity	NPC473179
0.7972	Intermediate Similarity	NPC473181
0.7972	Intermediate Similarity	NPC187558
0.7965	Intermediate Similarity	NPC101350
0.7953	Intermediate Similarity	NPC475070
0.7951	Intermediate Similarity	NPC284678
0.7948	Intermediate Similarity	NPC141053
0.7945	Intermediate Similarity	NPC473180
0.7933	Intermediate Similarity	NPC76748
0.7926	Intermediate Similarity	NPC287208
0.7922	Intermediate Similarity	NPC235685
0.7905	Intermediate Similarity	NPC307963
0.7895	Intermediate Similarity	NPC92111
0.7885	Intermediate Similarity	NPC296527
0.7845	Intermediate Similarity	NPC473183
0.7835	Intermediate Similarity	NPC39370
0.783	Intermediate Similarity	NPC251090
0.7826	Intermediate Similarity	NPC473186
0.7822	Intermediate Similarity	NPC60621
0.7807	Intermediate Similarity	NPC6215
0.7799	Intermediate Similarity	NPC242928
0.7788	Intermediate Similarity	NPC118832
0.7788	Intermediate Similarity	NPC165349
0.7788	Intermediate Similarity	NPC329708
0.7788	Intermediate Similarity	NPC264166
0.7788	Intermediate Similarity	NPC274291
0.7788	Intermediate Similarity	NPC47059
0.7783	Intermediate Similarity	NPC260434
0.7769	Intermediate Similarity	NPC258048
0.7767	Intermediate Similarity	NPC315957
0.7763	Intermediate Similarity	NPC82548
0.7759	Intermediate Similarity	NPC473184
0.7752	Intermediate Similarity	NPC472111
0.7727	Intermediate Similarity	NPC469589
0.7721	Intermediate Similarity	NPC128823
0.7721	Intermediate Similarity	NPC18487
0.7712	Intermediate Similarity	NPC473312
0.7699	Intermediate Similarity	NPC63971
0.7699	Intermediate Similarity	NPC91868
0.7685	Intermediate Similarity	NPC329793
0.7685	Intermediate Similarity	NPC121772
0.7681	Intermediate Similarity	NPC474798
0.7675	Intermediate Similarity	NPC122436
0.7664	Intermediate Similarity	NPC13880
0.7647	Intermediate Similarity	NPC174672
0.7647	Intermediate Similarity	NPC472434
0.7647	Intermediate Similarity	NPC174758
0.7607	Intermediate Similarity	NPC182222
0.7606	Intermediate Similarity	NPC324149
0.76	Intermediate Similarity	NPC288349
0.76	Intermediate Similarity	NPC477110
0.7589	Intermediate Similarity	NPC266931
0.7585	Intermediate Similarity	NPC11408
0.7566	Intermediate Similarity	NPC305984
0.7565	Intermediate Similarity	NPC21638
0.7564	Intermediate Similarity	NPC473182
0.756	Intermediate Similarity	NPC176127
0.7555	Intermediate Similarity	NPC470501
0.7545	Intermediate Similarity	NPC16452
0.7545	Intermediate Similarity	NPC470930
0.7545	Intermediate Similarity	NPC36229
0.7545	Intermediate Similarity	NPC476581
0.7532	Intermediate Similarity	NPC227908
0.7523	Intermediate Similarity	NPC475910
0.7523	Intermediate Similarity	NPC477111
0.7523	Intermediate Similarity	NPC329747
0.7523	Intermediate Similarity	NPC249040
0.7523	Intermediate Similarity	NPC476465
0.7522	Intermediate Similarity	NPC251936
0.7521	Intermediate Similarity	NPC217554
0.7511	Intermediate Similarity	NPC234078
0.7511	Intermediate Similarity	NPC162530
0.7511	Intermediate Similarity	NPC41679
0.7511	Intermediate Similarity	NPC221100
0.7511	Intermediate Similarity	NPC471506
0.7511	Intermediate Similarity	NPC470502
0.75	Intermediate Similarity	NPC284141
0.7489	Intermediate Similarity	NPC476116
0.7488	Intermediate Similarity	NPC226202
0.7478	Intermediate Similarity	NPC280272
0.7477	Intermediate Similarity	NPC4071
0.7477	Intermediate Similarity	NPC476582
0.7477	Intermediate Similarity	NPC476578
0.7477	Intermediate Similarity	NPC287437
0.7476	Intermediate Similarity	NPC48938
0.7468	Intermediate Similarity	NPC15801
0.7468	Intermediate Similarity	NPC184680
0.7467	Intermediate Similarity	NPC96405
0.7467	Intermediate Similarity	NPC86078
0.7467	Intermediate Similarity	NPC53069
0.7467	Intermediate Similarity	NPC202768
0.7467	Intermediate Similarity	NPC316981
0.7467	Intermediate Similarity	NPC296482
0.7467	Intermediate Similarity	NPC171409
0.7455	Intermediate Similarity	NPC11464
0.7446	Intermediate Similarity	NPC470503
0.7445	Intermediate Similarity	NPC152768
0.7445	Intermediate Similarity	NPC472027
0.7445	Intermediate Similarity	NPC274982
0.7445	Intermediate Similarity	NPC148183
0.7442	Intermediate Similarity	NPC99666
0.7441	Intermediate Similarity	NPC84478
0.7437	Intermediate Similarity	NPC470785
0.7437	Intermediate Similarity	NPC30540
0.7434	Intermediate Similarity	NPC473757
0.7429	Intermediate Similarity	NPC161887
0.7425	Intermediate Similarity	NPC476492
0.7409	Intermediate Similarity	NPC31930
0.7407	Intermediate Similarity	NPC198673
0.7407	Intermediate Similarity	NPC475190
0.7406	Intermediate Similarity	NPC20249
0.7399	Intermediate Similarity	NPC135549
0.7399	Intermediate Similarity	NPC313189
0.7393	Intermediate Similarity	NPC253580
0.7391	Intermediate Similarity	NPC477533
0.7391	Intermediate Similarity	NPC472099
0.7389	Intermediate Similarity	NPC472098
0.7384	Intermediate Similarity	NPC24802
0.7382	Intermediate Similarity	NPC202503
0.7379	Intermediate Similarity	NPC472436
0.7378	Intermediate Similarity	NPC471304
0.7376	Intermediate Similarity	NPC473761
0.7375	Intermediate Similarity	NPC477066
0.7375	Intermediate Similarity	NPC99891
0.7373	Intermediate Similarity	NPC131017
0.7373	Intermediate Similarity	NPC207686
0.7364	Intermediate Similarity	NPC234197
0.7364	Intermediate Similarity	NPC470784
0.7361	Intermediate Similarity	NPC195268
0.7361	Intermediate Similarity	NPC133140
0.7357	Intermediate Similarity	NPC478074
0.7354	Intermediate Similarity	NPC470164
0.7354	Intermediate Similarity	NPC323345
0.7354	Intermediate Similarity	NPC477113
0.7352	Intermediate Similarity	NPC168911
0.735	Intermediate Similarity	NPC470126
0.7346	Intermediate Similarity	NPC219963
0.7344	Intermediate Similarity	NPC478081
0.7344	Intermediate Similarity	NPC478082
0.7344	Intermediate Similarity	NPC477067
0.7342	Intermediate Similarity	NPC162484
0.7342	Intermediate Similarity	NPC329631
0.7328	Intermediate Similarity	NPC472435
0.7324	Intermediate Similarity	NPC314002
0.7324	Intermediate Similarity	NPC15102
0.7313	Intermediate Similarity	NPC112206
0.7313	Intermediate Similarity	NPC118940
0.7313	Intermediate Similarity	NPC202605
0.7309	Intermediate Similarity	NPC470505

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 NPC469554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	658
0.2-0.3	875
0.3-0.4	1880
0.4-0.5	2461
0.5-0.6	1912
0.6-0.7	850
0.7-0.8	150
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
0.8043	Intermediate Similarity	NPD5482	Discontinued
0.8026	Intermediate Similarity	NPD7558	Phase 2
0.8026	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1038	Approved
0.7879	Intermediate Similarity	NPD3006	Discontinued
0.7875	Intermediate Similarity	NPD6961	Discontinued
0.7873	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD4795	Phase 2
0.7869	Intermediate Similarity	NPD3343	Phase 3
0.7851	Intermediate Similarity	NPD5559	Phase 2
0.7844	Intermediate Similarity	NPD5658	Approved
0.7788	Intermediate Similarity	NPD4035	Approved
0.7788	Intermediate Similarity	NPD4034	Approved
0.7788	Intermediate Similarity	NPD1856	Discontinued
0.7788	Intermediate Similarity	NPD4036	Approved
0.7788	Intermediate Similarity	NPD4033	Approved
0.7788	Intermediate Similarity	NPD31	Approved
0.7788	Intermediate Similarity	NPD4038	Approved
0.7788	Intermediate Similarity	NPD32	Approved
0.7788	Intermediate Similarity	NPD4037	Approved
0.7788	Intermediate Similarity	NPD4122	Approved
0.7788	Intermediate Similarity	NPD4039	Approved
0.7767	Intermediate Similarity	NPD1739	Approved
0.7767	Intermediate Similarity	NPD1740	Approved
0.7758	Intermediate Similarity	NPD5612	Discontinued
0.7733	Intermediate Similarity	NPD3402	Phase 1
0.7724	Intermediate Similarity	NPD5450	Discontinued
0.7721	Intermediate Similarity	NPD3825	Phase 3
0.768	Intermediate Similarity	NPD5018	Phase 3
0.7664	Intermediate Similarity	NPD3477	Phase 2
0.7664	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4502	Phase 2
0.7655	Intermediate Similarity	NPD7194	Discontinued
0.7639	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1392	Approved
0.7617	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7603	Discontinued
0.7605	Intermediate Similarity	NPD7068	Approved
0.7605	Intermediate Similarity	NPD7067	Approved
0.7591	Intermediate Similarity	NPD3003	Approved
0.7578	Intermediate Similarity	NPD5067	Phase 2
0.7578	Intermediate Similarity	NPD5066	Phase 2
0.7564	Intermediate Similarity	NPD6494	Phase 2
0.7557	Intermediate Similarity	NPD7222	Phase 2
0.7556	Intermediate Similarity	NPD5902	Approved
0.7556	Intermediate Similarity	NPD5903	Approved
0.7541	Intermediate Similarity	NPD8442	Discontinued
0.7533	Intermediate Similarity	NPD4429	Discontinued
0.7523	Intermediate Similarity	NPD6569	Phase 2
0.7523	Intermediate Similarity	NPD2187	Approved
0.7523	Intermediate Similarity	NPD2189	Approved
0.75	Intermediate Similarity	NPD4131	Phase 3
0.75	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1034	Phase 3
0.748	Intermediate Similarity	NPD4442	Phase 2
0.7479	Intermediate Similarity	NPD4858	Phase 2
0.7477	Intermediate Similarity	NPD4548	Discontinued
0.7467	Intermediate Similarity	NPD3815	Phase 1
0.7467	Intermediate Similarity	NPD3816	Phase 1
0.7467	Intermediate Similarity	NPD6242	Discontinued
0.7449	Intermediate Similarity	NPD6243	Phase 3
0.7449	Intermediate Similarity	NPD6244	Phase 3
0.7444	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6968	Phase 2
0.7436	Intermediate Similarity	NPD6969	Phase 2
0.7432	Intermediate Similarity	NPD8403	Phase 1
0.7432	Intermediate Similarity	NPD5530	Phase 1
0.7407	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5644	Phase 1
0.7395	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4343	Phase 1
0.7391	Intermediate Similarity	NPD5930	Phase 3
0.7389	Intermediate Similarity	NPD3330	Phase 1
0.7388	Intermediate Similarity	NPD7659	Discontinued
0.7385	Intermediate Similarity	NPD7948	Phase 1
0.738	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD4885	Approved
0.7373	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6306	Phase 2
0.7371	Intermediate Similarity	NPD5256	Discontinued
0.7368	Intermediate Similarity	NPD6643	Discontinued
0.7364	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3924	Approved
0.7361	Intermediate Similarity	NPD3921	Approved
0.7361	Intermediate Similarity	NPD3923	Approved
0.7361	Intermediate Similarity	NPD3922	Approved
0.7359	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4454	Phase 2
0.735	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3875	Discontinued
0.7342	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD4558	Phase 2
0.7333	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7331	Intermediate Similarity	NPD6131	Phase 1
0.7328	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD8100	Phase 3
0.7321	Intermediate Similarity	NPD7452	Approved
0.7321	Intermediate Similarity	NPD7453	Approved
0.7318	Intermediate Similarity	NPD1768	Approved
0.7318	Intermediate Similarity	NPD5999	Phase 2
0.7317	Intermediate Similarity	NPD7859	Phase 2
0.7308	Intermediate Similarity	NPD7675	Phase 3
0.7308	Intermediate Similarity	NPD7426	Phase 1
0.7308	Intermediate Similarity	NPD7674	Phase 3
0.7308	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6985	Discontinued
0.7298	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5022	Discontinued
0.7288	Intermediate Similarity	NPD8512	Phase 3
0.7281	Intermediate Similarity	NPD4372	Phase 1
0.7276	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7221	Approved
0.7253	Intermediate Similarity	NPD7219	Approved
0.7243	Intermediate Similarity	NPD5802	Phase 2
0.724	Intermediate Similarity	NPD2175	Phase 3
0.724	Intermediate Similarity	NPD2177	Approved
0.724	Intermediate Similarity	NPD2176	Approved
0.7238	Intermediate Similarity	NPD6963	Approved
0.7238	Intermediate Similarity	NPD6964	Approved
0.7236	Intermediate Similarity	NPD8101	Phase 3
0.7235	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5913	Phase 3
0.7233	Intermediate Similarity	NPD8284	Discontinued
0.7224	Intermediate Similarity	NPD8358	Approved
0.7215	Intermediate Similarity	NPD5479	Discontinued
0.7209	Intermediate Similarity	NPD4919	Phase 3
0.7209	Intermediate Similarity	NPD4921	Phase 3
0.7209	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6473	Phase 1
0.7198	Intermediate Similarity	NPD3763	Approved
0.7196	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5939	Approved
0.7193	Intermediate Similarity	NPD3939	Suspended
0.7193	Intermediate Similarity	NPD5936	Approved
0.7189	Intermediate Similarity	NPD8246	Approved
0.7189	Intermediate Similarity	NPD8063	Discontinued
0.7189	Intermediate Similarity	NPD8247	Approved
0.7188	Intermediate Similarity	NPD4886	Phase 2
0.7172	Intermediate Similarity	NPD6573	Phase 3
0.7172	Intermediate Similarity	NPD6572	Phase 2
0.7171	Intermediate Similarity	NPD112	Approved
0.7171	Intermediate Similarity	NPD9705	Discontinued
0.7169	Intermediate Similarity	NPD802	Phase 2
0.7168	Intermediate Similarity	NPD6290	Phase 2
0.7166	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5632	Approved
0.7155	Intermediate Similarity	NPD5948	Phase 2
0.7149	Intermediate Similarity	NPD6750	Phase 2
0.7136	Intermediate Similarity	NPD6595	Phase 3
0.7124	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3570	Phase 2
0.7118	Intermediate Similarity	NPD949	Phase 1
0.7105	Intermediate Similarity	NPD4437	Phase 3
0.7104	Intermediate Similarity	NPD6550	Discontinued
0.7103	Intermediate Similarity	NPD7956	Approved
0.7103	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7955	Approved
0.7094	Intermediate Similarity	NPD6856	Discontinued
0.7094	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8525	Approved
0.7092	Intermediate Similarity	NPD8244	Phase 2
0.7089	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7051	Phase 3
0.7083	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6531	Approved
0.7075	Intermediate Similarity	NPD6530	Approved
0.7073	Intermediate Similarity	NPD6230	Discontinued
0.7072	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7726	Phase 1
0.7061	Intermediate Similarity	NPD5529	Phase 1
0.7061	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4418	Discontinued
0.7054	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6500	Approved
0.7051	Intermediate Similarity	NPD6501	Approved
0.7048	Intermediate Similarity	NPD565	Phase 2
0.7043	Intermediate Similarity	NPD7470	Discontinued
0.7043	Intermediate Similarity	NPD6220	Phase 3
0.7042	Intermediate Similarity	NPD2062	Phase 2
0.7039	Intermediate Similarity	NPD5164	Discontinued
0.7034	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7413	Phase 3
0.7025	Intermediate Similarity	NPD2757	Phase 2
0.7024	Intermediate Similarity	NPD8049	Phase 2
0.7023	Intermediate Similarity	NPD4204	Approved
0.7023	Intermediate Similarity	NPD4203	Approved
0.7018	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3254	Phase 1
0.7016	Intermediate Similarity	NPD3255	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