NPASS Compound

Structure

CID32002 OpenBabel06191715362D 27 27 0 0 1 0 0 0 0 0999 V2000 3.9641 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8301 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.2942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 16 2 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	274.12
Volume:	289.565
LogP:	3.499
LogD:	2.921
LogS:	-3.619
# Rotatable Bonds:	5
TPSA:	16.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	2.471
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.328
MDCK Permeability:	1.181614788947627e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	76.2685775756836%
Volume Distribution (VD):	3.941
Pgp-substrate:	28.54267692565918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.979
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.376
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	6.299
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.471
Human Hepatotoxicity (H-HT):	0.647
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.21
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC32002

Natural Product ID:	NPC32002
*Common Name:**	Chlorphenamine Maleate
IUPAC Name:	(E)-but-2-enedioic acid;3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
Synonyms:
Standard InCHIKey:	DBAKFASWICGISY-WLHGVMLRSA-N
Standard InCHI:	InChI=1S/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
SMILES:	CN(CCC(c1ccccn1)c1ccc(cc1)Cl)C.OC(=O)/C=C/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL180454
PubChem CID:	6433151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0000184] Pheniramines

*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
NPO8070	Chlorpheniramini maleas	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO8070	Chlorpheniramini maleas	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	4
Potency	5

Activity Type	# Activity
Cell Line	1
Individual Protein	3
ORGANISM	3
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[536210]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[536210]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	920.0	nM	PMID[536210]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[536210]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[536210]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	5.64	%	PMID[536211]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.683	%	PMID[536212]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.18	%	PMID[536213]

☑ 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 NPC32002 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	282
0.1-0.2	3113
0.2-0.3	13749
0.3-0.4	18099
0.4-0.5	3801
0.5-0.6	2372
0.6-0.7	1186
0.7-0.8	92
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC315348
0.8707	High Similarity	NPC476464
0.8451	Intermediate Similarity	NPC316811
0.8442	Intermediate Similarity	NPC116961
0.844	Intermediate Similarity	NPC314102
0.844	Intermediate Similarity	NPC251722
0.8344	Intermediate Similarity	NPC477591
0.8333	Intermediate Similarity	NPC91958
0.8258	Intermediate Similarity	NPC297486
0.8258	Intermediate Similarity	NPC240136
0.8258	Intermediate Similarity	NPC471402
0.8207	Intermediate Similarity	NPC476454
0.8182	Intermediate Similarity	NPC471312
0.8162	Intermediate Similarity	NPC46358
0.8102	Intermediate Similarity	NPC476322
0.8088	Intermediate Similarity	NPC329825
0.806	Intermediate Similarity	NPC143603
0.8056	Intermediate Similarity	NPC150259
0.8029	Intermediate Similarity	NPC290094
0.8015	Intermediate Similarity	NPC265605
0.8015	Intermediate Similarity	NPC182570
0.8015	Intermediate Similarity	NPC48564
0.7958	Intermediate Similarity	NPC256893
0.7895	Intermediate Similarity	NPC470233
0.7887	Intermediate Similarity	NPC282398
0.7887	Intermediate Similarity	NPC69914
0.7863	Intermediate Similarity	NPC27802
0.7857	Intermediate Similarity	NPC202957
0.7857	Intermediate Similarity	NPC169625
0.7829	Intermediate Similarity	NPC40070
0.7823	Intermediate Similarity	NPC73767
0.7817	Intermediate Similarity	NPC475105
0.7817	Intermediate Similarity	NPC476131
0.7817	Intermediate Similarity	NPC329896
0.7817	Intermediate Similarity	NPC475090
0.7815	Intermediate Similarity	NPC470111
0.7786	Intermediate Similarity	NPC166424
0.7786	Intermediate Similarity	NPC245244
0.7786	Intermediate Similarity	NPC146373
0.777	Intermediate Similarity	NPC469783
0.777	Intermediate Similarity	NPC469768
0.777	Intermediate Similarity	NPC469780
0.777	Intermediate Similarity	NPC469779
0.777	Intermediate Similarity	NPC469761
0.777	Intermediate Similarity	NPC469767
0.777	Intermediate Similarity	NPC469784
0.7755	Intermediate Similarity	NPC169433
0.7746	Intermediate Similarity	NPC89490
0.7721	Intermediate Similarity	NPC81561
0.7718	Intermediate Similarity	NPC469766
0.7708	Intermediate Similarity	NPC101165
0.7703	Intermediate Similarity	NPC110126
0.7687	Intermediate Similarity	NPC84911
0.7647	Intermediate Similarity	NPC476566
0.7647	Intermediate Similarity	NPC148140
0.7643	Intermediate Similarity	NPC56765
0.7636	Intermediate Similarity	NPC314919
0.7634	Intermediate Similarity	NPC231655
0.7634	Intermediate Similarity	NPC76540
0.7619	Intermediate Similarity	NPC261195
0.7619	Intermediate Similarity	NPC96102
0.7619	Intermediate Similarity	NPC29886
0.7597	Intermediate Similarity	NPC53947
0.7589	Intermediate Similarity	NPC27740
0.7584	Intermediate Similarity	NPC104483
0.7582	Intermediate Similarity	NPC201380
0.7582	Intermediate Similarity	NPC179787
0.758	Intermediate Similarity	NPC129721
0.7568	Intermediate Similarity	NPC105127
0.7566	Intermediate Similarity	NPC86288
0.7552	Intermediate Similarity	NPC471313
0.7552	Intermediate Similarity	NPC471311
0.755	Intermediate Similarity	NPC20144
0.7533	Intermediate Similarity	NPC59084
0.7532	Intermediate Similarity	NPC321911
0.7516	Intermediate Similarity	NPC63545
0.7516	Intermediate Similarity	NPC51054
0.75	Intermediate Similarity	NPC90723
0.7483	Intermediate Similarity	NPC63157
0.7483	Intermediate Similarity	NPC473868
0.7468	Intermediate Similarity	NPC469811
0.7451	Intermediate Similarity	NPC314372
0.7434	Intermediate Similarity	NPC190296
0.7432	Intermediate Similarity	NPC198988
0.7429	Intermediate Similarity	NPC215519
0.7421	Intermediate Similarity	NPC318065
0.7421	Intermediate Similarity	NPC206819
0.7417	Intermediate Similarity	NPC2949
0.7417	Intermediate Similarity	NPC279081
0.741	Intermediate Similarity	NPC162689
0.741	Intermediate Similarity	NPC54102
0.7403	Intermediate Similarity	NPC288838
0.7391	Intermediate Similarity	NPC478182
0.7389	Intermediate Similarity	NPC325903
0.7372	Intermediate Similarity	NPC24678
0.7372	Intermediate Similarity	NPC105818
0.7358	Intermediate Similarity	NPC286427
0.7355	Intermediate Similarity	NPC477974
0.7353	Intermediate Similarity	NPC235843
0.7347	Intermediate Similarity	NPC82295
0.7347	Intermediate Similarity	NPC471322
0.7343	Intermediate Similarity	NPC122718
0.7338	Intermediate Similarity	NPC285731
0.7312	Intermediate Similarity	NPC41257
0.7303	Intermediate Similarity	NPC230002
0.729	Intermediate Similarity	NPC143872
0.7278	Intermediate Similarity	NPC259644
0.7278	Intermediate Similarity	NPC469786
0.7278	Intermediate Similarity	NPC469765
0.7278	Intermediate Similarity	NPC200214
0.7278	Intermediate Similarity	NPC138842
0.7278	Intermediate Similarity	NPC25008
0.7278	Intermediate Similarity	NPC469760
0.7278	Intermediate Similarity	NPC73952
0.7278	Intermediate Similarity	NPC469763
0.7267	Intermediate Similarity	NPC215584
0.7267	Intermediate Similarity	NPC325252
0.7267	Intermediate Similarity	NPC44773
0.725	Intermediate Similarity	NPC236711
0.725	Intermediate Similarity	NPC216643
0.7244	Intermediate Similarity	NPC21605
0.7244	Intermediate Similarity	NPC471957
0.7237	Intermediate Similarity	NPC88097
0.7235	Intermediate Similarity	NPC83381
0.7233	Intermediate Similarity	NPC80597
0.7233	Intermediate Similarity	NPC75540
0.7233	Intermediate Similarity	NPC70922
0.7233	Intermediate Similarity	NPC211572
0.7233	Intermediate Similarity	NPC212376
0.723	Intermediate Similarity	NPC324611
0.7226	Intermediate Similarity	NPC159856
0.7222	Intermediate Similarity	NPC470203
0.7219	Intermediate Similarity	NPC65408
0.7205	Intermediate Similarity	NPC293487
0.72	Intermediate Similarity	NPC315617
0.72	Intermediate Similarity	NPC314058
0.72	Intermediate Similarity	NPC316018
0.72	Intermediate Similarity	NPC316359
0.7176	Intermediate Similarity	NPC83987
0.7169	Intermediate Similarity	NPC201634
0.7162	Intermediate Similarity	NPC22079
0.716	Intermediate Similarity	NPC470204
0.7152	Intermediate Similarity	NPC33421
0.7143	Intermediate Similarity	NPC167635
0.7143	Intermediate Similarity	NPC280852
0.7143	Intermediate Similarity	NPC193740
0.7125	Intermediate Similarity	NPC34844
0.7108	Intermediate Similarity	NPC194411
0.7107	Intermediate Similarity	NPC470823
0.7099	Intermediate Similarity	NPC80681
0.7099	Intermediate Similarity	NPC92796
0.7099	Intermediate Similarity	NPC135141
0.7097	Intermediate Similarity	NPC477977
0.7091	Intermediate Similarity	NPC49954
0.7091	Intermediate Similarity	NPC474561
0.7091	Intermediate Similarity	NPC478183
0.7081	Intermediate Similarity	NPC115049
0.7081	Intermediate Similarity	NPC469785
0.7075	Intermediate Similarity	NPC278451
0.7073	Intermediate Similarity	NPC478184
0.7073	Intermediate Similarity	NPC317105
0.7066	Intermediate Similarity	NPC82331
0.7063	Intermediate Similarity	NPC141926
0.7055	Intermediate Similarity	NPC122141
0.7041	Intermediate Similarity	NPC474958
0.7041	Intermediate Similarity	NPC203754
0.7041	Intermediate Similarity	NPC150048
0.7037	Intermediate Similarity	NPC469762
0.7023	Intermediate Similarity	NPC213774
0.7019	Intermediate Similarity	NPC476219
0.7019	Intermediate Similarity	NPC476297
0.7012	Intermediate Similarity	NPC225018
0.7012	Intermediate Similarity	NPC478185
0.7007	Intermediate Similarity	NPC476140
0.7006	Intermediate Similarity	NPC469525
0.7006	Intermediate Similarity	NPC470440
0.7006	Intermediate Similarity	NPC91895
0.7	Intermediate Similarity	NPC475450
0.7	Intermediate Similarity	NPC216713
0.6988	Remote Similarity	NPC160105
0.6988	Remote Similarity	NPC98187
0.6988	Remote Similarity	NPC56233
0.6982	Remote Similarity	NPC37423
0.6982	Remote Similarity	NPC275305
0.697	Remote Similarity	NPC311276
0.697	Remote Similarity	NPC265100
0.6968	Remote Similarity	NPC115611
0.6959	Remote Similarity	NPC248462
0.6946	Remote Similarity	NPC201700
0.694	Remote Similarity	NPC471617
0.6933	Remote Similarity	NPC475428
0.6933	Remote Similarity	NPC469897
0.6928	Remote Similarity	NPC218268
0.6928	Remote Similarity	NPC274229
0.6914	Remote Similarity	NPC229055
0.6909	Remote Similarity	NPC124542
0.6909	Remote Similarity	NPC59779
0.6909	Remote Similarity	NPC471177
0.6909	Remote Similarity	NPC282231
0.6905	Remote Similarity	NPC32534

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 NPC32002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	679
0.2-0.3	896
0.3-0.4	1541
0.4-0.5	2745
0.5-0.6	2235
0.6-0.7	786
0.7-0.8	95
0.8-0.85	3
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2073	Approved
1.0	High Similarity	NPD2075	Approved
1.0	High Similarity	NPD2074	Approved
1.0	High Similarity	NPD2072	Approved
0.916	High Similarity	NPD2119	Approved
0.916	High Similarity	NPD2118	Approved
0.8904	High Similarity	NPD6497	Approved
0.8828	High Similarity	NPD3339	Approved
0.8767	High Similarity	NPD2165	Phase 1
0.8759	High Similarity	NPD4029	Approved
0.8759	High Similarity	NPD4030	Approved
0.8759	High Similarity	NPD4028	Approved
0.8725	High Similarity	NPD4384	Clinical (unspecified phase)
0.8707	High Similarity	NPD3115	Approved
0.8707	High Similarity	NPD3112	Approved
0.8707	High Similarity	NPD3114	Approved
0.8707	High Similarity	NPD3113	Approved
0.8676	High Similarity	NPD3476	Approved
0.8676	High Similarity	NPD3475	Approved
0.8649	High Similarity	NPD2865	Clinical (unspecified phase)
0.8623	High Similarity	NPD3942	Approved
0.8623	High Similarity	NPD3944	Approved
0.8553	High Similarity	NPD3929	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD2069	Approved
0.8451	Intermediate Similarity	NPD2068	Approved
0.8451	Intermediate Similarity	NPD2070	Approved
0.8451	Intermediate Similarity	NPD2071	Approved
0.8451	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD4973	Approved
0.8425	Intermediate Similarity	NPD2110	Approved
0.8321	Intermediate Similarity	NPD991	Phase 2
0.8321	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2077	Approved
0.8217	Intermediate Similarity	NPD2076	Approved
0.8153	Intermediate Similarity	NPD3117	Approved
0.8153	Intermediate Similarity	NPD3116	Approved
0.8116	Intermediate Similarity	NPD9583	Approved
0.8113	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD1993	Approved
0.8028	Intermediate Similarity	NPD1995	Approved
0.8028	Intermediate Similarity	NPD1994	Approved
0.8027	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD268	Approved
0.8015	Intermediate Similarity	NPD271	Approved
0.8015	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD715	Phase 3
0.7987	Intermediate Similarity	NPD7216	Approved
0.7987	Intermediate Similarity	NPD7217	Approved
0.7971	Intermediate Similarity	NPD9357	Approved
0.7959	Intermediate Similarity	NPD1722	Approved
0.7933	Intermediate Similarity	NPD4702	Approved
0.7933	Intermediate Similarity	NPD4547	Phase 3
0.7933	Intermediate Similarity	NPD4703	Approved
0.7867	Intermediate Similarity	NPD7469	Discontinued
0.7847	Intermediate Similarity	NPD3385	Approved
0.7785	Intermediate Similarity	NPD2006	Phase 2
0.7778	Intermediate Similarity	NPD2771	Approved
0.7763	Intermediate Similarity	NPD2430	Phase 2
0.7744	Intermediate Similarity	NPD4823	Approved
0.7744	Intermediate Similarity	NPD4824	Approved
0.7733	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6217	Discontinued
0.7711	Intermediate Similarity	NPD5892	Approved
0.7703	Intermediate Similarity	NPD786	Approved
0.7692	Intermediate Similarity	NPD2373	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3654	Approved
0.7676	Intermediate Similarity	NPD1598	Discontinued
0.7671	Intermediate Similarity	NPD2140	Approved
0.7671	Intermediate Similarity	NPD2142	Approved
0.7671	Intermediate Similarity	NPD2141	Approved
0.7647	Intermediate Similarity	NPD3100	Discontinued
0.7634	Intermediate Similarity	NPD9098	Phase 3
0.7634	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2837	Discontinued
0.7591	Intermediate Similarity	NPD9396	Approved
0.7591	Intermediate Similarity	NPD9392	Approved
0.758	Intermediate Similarity	NPD2582	Approved
0.758	Intermediate Similarity	NPD2581	Approved
0.7574	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3717	Discontinued
0.755	Intermediate Similarity	NPD4510	Discontinued
0.7547	Intermediate Similarity	NPD5315	Discontinued
0.7532	Intermediate Similarity	NPD5255	Approved
0.753	Intermediate Similarity	NPD3927	Phase 2
0.7516	Intermediate Similarity	NPD1248	Discontinued
0.75	Intermediate Similarity	NPD792	Discontinued
0.75	Intermediate Similarity	NPD3323	Discontinued
0.75	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4891	Phase 2
0.7485	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2466	Phase 3
0.7484	Intermediate Similarity	NPD2462	Phase 3
0.7484	Intermediate Similarity	NPD2465	Approved
0.7434	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2896	Discontinued
0.7386	Intermediate Similarity	NPD3813	Approved
0.7384	Intermediate Similarity	NPD6133	Discontinued
0.7372	Intermediate Similarity	NPD2172	Phase 1
0.7362	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2641	Approved
0.7362	Intermediate Similarity	NPD2640	Approved
0.7356	Intermediate Similarity	NPD4528	Approved
0.7356	Intermediate Similarity	NPD4526	Approved
0.7356	Intermediate Similarity	NPD4529	Approved
0.7355	Intermediate Similarity	NPD1661	Suspended
0.7353	Intermediate Similarity	NPD3771	Phase 3
0.7342	Intermediate Similarity	NPD977	Approved
0.7342	Intermediate Similarity	NPD976	Approved
0.7342	Intermediate Similarity	NPD975	Approved
0.7333	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD45	Approved
0.7333	Intermediate Similarity	NPD4524	Discontinued
0.7333	Intermediate Similarity	NPD6554	Approved
0.7329	Intermediate Similarity	NPD6771	Discontinued
0.7325	Intermediate Similarity	NPD4641	Discontinued
0.7308	Intermediate Similarity	NPD1183	Approved
0.7305	Intermediate Similarity	NPD2731	Phase 2
0.7297	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2580	Discontinued
0.729	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1380	Discovery
0.7273	Intermediate Similarity	NPD3610	Approved
0.7273	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3609	Approved
0.7267	Intermediate Similarity	NPD1255	Approved
0.7267	Intermediate Similarity	NPD1254	Approved
0.7267	Intermediate Similarity	NPD1253	Approved
0.7267	Intermediate Similarity	NPD1256	Approved
0.7255	Intermediate Similarity	NPD5020	Approved
0.7246	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD409	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1937	Approved
0.7219	Intermediate Similarity	NPD200	Phase 2
0.7219	Intermediate Similarity	NPD201	Phase 2
0.7205	Intermediate Similarity	NPD5418	Discontinued
0.719	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD165	Phase 2
0.7179	Intermediate Similarity	NPD1683	Approved
0.7175	Intermediate Similarity	NPD4848	Phase 1
0.7163	Intermediate Similarity	NPD3499	Approved
0.7163	Intermediate Similarity	NPD3498	Approved
0.7161	Intermediate Similarity	NPD5671	Approved
0.7161	Intermediate Similarity	NPD4509	Discontinued
0.716	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2511	Approved
0.7153	Intermediate Similarity	NPD2940	Approved
0.7153	Intermediate Similarity	NPD2938	Approved
0.7152	Intermediate Similarity	NPD4639	Approved
0.7152	Intermediate Similarity	NPD5862	Discovery
0.7152	Intermediate Similarity	NPD4638	Approved
0.7152	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4640	Approved
0.7143	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1383	Phase 3
0.7143	Intermediate Similarity	NPD1382	Phase 2
0.7143	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5213	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2730	Approved
0.7126	Intermediate Similarity	NPD2728	Approved
0.7126	Intermediate Similarity	NPD2729	Approved
0.7125	Intermediate Similarity	NPD2809	Approved
0.7118	Intermediate Similarity	NPD6514	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6515	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5400	Approved
0.7114	Intermediate Similarity	NPD803	Phase 1
0.7107	Intermediate Similarity	NPD3262	Approved
0.7101	Intermediate Similarity	NPD7111	Discontinued
0.7101	Intermediate Similarity	NPD4181	Approved
0.7099	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3361	Phase 1
0.7089	Intermediate Similarity	NPD3852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1561	Phase 2
0.7083	Intermediate Similarity	NPD5787	Discontinued
0.7076	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3583	Phase 2
0.7069	Intermediate Similarity	NPD2770	Discontinued
0.7066	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5472	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1404	Approved
0.7055	Intermediate Similarity	NPD1403	Approved
0.7052	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5254	Discontinued
0.7045	Intermediate Similarity	NPD4699	Discontinued
0.7035	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6194	Discontinued
0.7033	Intermediate Similarity	NPD3931	Approved
0.7033	Intermediate Similarity	NPD3928	Approved
0.703	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2782	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data