NPASS Compound

Structure

CID255253 OpenBabel06191716062D 29 31 0 0 0 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -3.4641 -1.0000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 1.7321 -0.0000 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 0.8660 0.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 4.3301 -1.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 23 2 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 29 1 0 0 0 0 25 26 2 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	405.19
Volume:	441.216
LogP:	5.706
LogD:	5.159
LogS:	-5.603
# Rotatable Bonds:	9
TPSA:	12.47
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	2.135
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.476
MDCK Permeability:	1.5009635717433412e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	98.10802459716797%
Volume Distribution (VD):	1.222
Pgp-substrate:	1.0363404750823975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.715
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.434
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.993
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	8.643
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.77
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.423
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.414
Carcinogencity:	0.208
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC255253

Natural Product ID:	NPC255253
*Common Name:**	Zuclomiphene
IUPAC Name:	2-[4-[(Z)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
Synonyms:	Isomer A; RMI-16312; Transclomiphene; Zuclomifene; Zuclomiphene
Standard InCHIKey:	GKIRPKYJQBWNGO-QPLCGJKRSA-N
Standard InCHI:	InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25-
SMILES:	CCN(CC)CCOc1ccc(cc1)/C(=C(/c1ccccc1)Cl)/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL167779
PubChem CID:	1548955
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30892891]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1150	Juncus effusus	Species	Juncaceae	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
Ki	3
Others	2

Activity Type	# Activity
Individual Protein	5
Protein Family	1
Uncleic Acid	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4110	Individual Protein	3-beta-hydroxysteroid-delta(8),delta(7)-isomerase	Homo sapiens	Ki	=	2.0	nM	PMID[493842]
NPT296	Individual Protein	Sigma opioid receptor	Homo sapiens	Ki	=	5.0	nM	PMID[493842]
NPT4111	Individual Protein	C-8 sterol isomerase	Saccharomyces cerevisiae S288c	Ki	=	2.0	nM	PMID[493842]
NPT1881	Uncleic Acid	Calf thymus DNA	Bos taurus	rf50	=	20.0	n.a.	PMID[493841]
NPT3024	Protein Family	Estrogen receptor	Bos taurus	Relative affinity	=	0.0003	n.a.	PMID[493841]
NPT98	Individual Protein	HERG	Homo sapiens	IC50	=	181.97	nM	PMID[493843]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	IC50	=	37860.0	nM	PMID[493844]

☑ 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 NPC255253 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	221
0.1-0.2	1929
0.2-0.3	9967
0.3-0.4	8917
0.4-0.5	6342
0.5-0.6	11703
0.6-0.7	3467
0.7-0.8	148
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7863	Intermediate Similarity	NPC316797
0.7846	Intermediate Similarity	NPC328267
0.7845	Intermediate Similarity	NPC313918
0.7833	Intermediate Similarity	NPC326801
0.7812	Intermediate Similarity	NPC263835
0.7734	Intermediate Similarity	NPC256369
0.768	Intermediate Similarity	NPC26524
0.7676	Intermediate Similarity	NPC247298
0.7674	Intermediate Similarity	NPC321133
0.7627	Intermediate Similarity	NPC471576
0.7603	Intermediate Similarity	NPC470393
0.7594	Intermediate Similarity	NPC320242
0.7581	Intermediate Similarity	NPC95977
0.7576	Intermediate Similarity	NPC211218
0.7569	Intermediate Similarity	NPC245974
0.7541	Intermediate Similarity	NPC113457
0.7521	Intermediate Similarity	NPC108875
0.7521	Intermediate Similarity	NPC38079
0.7518	Intermediate Similarity	NPC189724
0.7518	Intermediate Similarity	NPC212850
0.7518	Intermediate Similarity	NPC83289
0.75	Intermediate Similarity	NPC474272
0.75	Intermediate Similarity	NPC300166
0.7462	Intermediate Similarity	NPC59561
0.7462	Intermediate Similarity	NPC172253
0.7462	Intermediate Similarity	NPC43275
0.7459	Intermediate Similarity	NPC473855
0.7438	Intermediate Similarity	NPC192596
0.7426	Intermediate Similarity	NPC283079
0.7422	Intermediate Similarity	NPC303370
0.7414	Intermediate Similarity	NPC321956
0.7391	Intermediate Similarity	NPC118419
0.7388	Intermediate Similarity	NPC62101
0.7388	Intermediate Similarity	NPC95733
0.7381	Intermediate Similarity	NPC166837
0.7355	Intermediate Similarity	NPC51633
0.7338	Intermediate Similarity	NPC325568
0.7333	Intermediate Similarity	NPC141739
0.7333	Intermediate Similarity	NPC136112
0.7333	Intermediate Similarity	NPC29477
0.7328	Intermediate Similarity	NPC71853
0.7317	Intermediate Similarity	NPC475269
0.7317	Intermediate Similarity	NPC42383
0.7308	Intermediate Similarity	NPC25648
0.7302	Intermediate Similarity	NPC475852
0.7288	Intermediate Similarity	NPC471581
0.728	Intermediate Similarity	NPC201959
0.728	Intermediate Similarity	NPC75440
0.728	Intermediate Similarity	NPC97811
0.7279	Intermediate Similarity	NPC218323
0.7266	Intermediate Similarity	NPC307123
0.7266	Intermediate Similarity	NPC274732
0.7266	Intermediate Similarity	NPC471953
0.7266	Intermediate Similarity	NPC97870
0.7266	Intermediate Similarity	NPC247018
0.7254	Intermediate Similarity	NPC318591
0.7254	Intermediate Similarity	NPC231163
0.725	Intermediate Similarity	NPC470161
0.725	Intermediate Similarity	NPC95755
0.7241	Intermediate Similarity	NPC259134
0.7241	Intermediate Similarity	NPC8002
0.7241	Intermediate Similarity	NPC99886
0.7241	Intermediate Similarity	NPC177844
0.7239	Intermediate Similarity	NPC100099
0.7239	Intermediate Similarity	NPC36016
0.7236	Intermediate Similarity	NPC241224
0.7234	Intermediate Similarity	NPC11147
0.7226	Intermediate Similarity	NPC172403
0.72	Intermediate Similarity	NPC157473
0.72	Intermediate Similarity	NPC151530
0.719	Intermediate Similarity	NPC100870
0.7185	Intermediate Similarity	NPC307020
0.7185	Intermediate Similarity	NPC38761
0.7185	Intermediate Similarity	NPC76465
0.7176	Intermediate Similarity	NPC323948
0.7164	Intermediate Similarity	NPC54972
0.7163	Intermediate Similarity	NPC29650
0.7154	Intermediate Similarity	NPC47194
0.7153	Intermediate Similarity	NPC304630
0.7153	Intermediate Similarity	NPC17837
0.7143	Intermediate Similarity	NPC146530
0.7143	Intermediate Similarity	NPC103916
0.7133	Intermediate Similarity	NPC193528
0.7132	Intermediate Similarity	NPC134195
0.7132	Intermediate Similarity	NPC294156
0.7132	Intermediate Similarity	NPC197351
0.7132	Intermediate Similarity	NPC106914
0.7132	Intermediate Similarity	NPC141003
0.7132	Intermediate Similarity	NPC86502
0.7132	Intermediate Similarity	NPC256015
0.7132	Intermediate Similarity	NPC165106
0.7132	Intermediate Similarity	NPC35344
0.7132	Intermediate Similarity	NPC246648
0.712	Intermediate Similarity	NPC92623
0.712	Intermediate Similarity	NPC135464
0.712	Intermediate Similarity	NPC176971
0.7113	Intermediate Similarity	NPC138365
0.7111	Intermediate Similarity	NPC150026
0.7111	Intermediate Similarity	NPC471315
0.7111	Intermediate Similarity	NPC471314
0.7109	Intermediate Similarity	NPC266932
0.7103	Intermediate Similarity	NPC470925
0.7099	Intermediate Similarity	NPC33900
0.7099	Intermediate Similarity	NPC9341
0.7099	Intermediate Similarity	NPC81067
0.7097	Intermediate Similarity	NPC283546
0.709	Intermediate Similarity	NPC83279
0.7087	Intermediate Similarity	NPC306045
0.7087	Intermediate Similarity	NPC265211
0.708	Intermediate Similarity	NPC102540
0.708	Intermediate Similarity	NPC285040
0.708	Intermediate Similarity	NPC17809
0.708	Intermediate Similarity	NPC103420
0.708	Intermediate Similarity	NPC188022
0.7073	Intermediate Similarity	NPC307425
0.7068	Intermediate Similarity	NPC163036
0.7068	Intermediate Similarity	NPC295259
0.7063	Intermediate Similarity	NPC42793
0.7063	Intermediate Similarity	NPC167944
0.7063	Intermediate Similarity	NPC231884
0.7063	Intermediate Similarity	NPC186469
0.7063	Intermediate Similarity	NPC258171
0.704	Intermediate Similarity	NPC128730
0.704	Intermediate Similarity	NPC233396
0.704	Intermediate Similarity	NPC154899
0.704	Intermediate Similarity	NPC8302
0.704	Intermediate Similarity	NPC473393
0.7037	Intermediate Similarity	NPC290451
0.7037	Intermediate Similarity	NPC127389
0.7034	Intermediate Similarity	NPC314682
0.7031	Intermediate Similarity	NPC88868
0.7031	Intermediate Similarity	NPC231251
0.7031	Intermediate Similarity	NPC25067
0.7031	Intermediate Similarity	NPC2682
0.7029	Intermediate Similarity	NPC230479
0.7029	Intermediate Similarity	NPC50315
0.7029	Intermediate Similarity	NPC301713
0.7029	Intermediate Similarity	NPC26879
0.7029	Intermediate Similarity	NPC276212
0.7029	Intermediate Similarity	NPC283049
0.7023	Intermediate Similarity	NPC475815
0.7023	Intermediate Similarity	NPC51345
0.7023	Intermediate Similarity	NPC473264
0.7021	Intermediate Similarity	NPC470392
0.7021	Intermediate Similarity	NPC474200
0.7015	Intermediate Similarity	NPC8283
0.7015	Intermediate Similarity	NPC258979
0.7015	Intermediate Similarity	NPC41801
0.7015	Intermediate Similarity	NPC93398
0.7008	Intermediate Similarity	NPC291837
0.7008	Intermediate Similarity	NPC309982
0.7	Intermediate Similarity	NPC90903
0.7	Intermediate Similarity	NPC474227
0.6992	Remote Similarity	NPC474040
0.6992	Remote Similarity	NPC107101
0.6992	Remote Similarity	NPC74821
0.6992	Remote Similarity	NPC474214
0.6986	Remote Similarity	NPC328750
0.6986	Remote Similarity	NPC188163
0.6986	Remote Similarity	NPC474915
0.6986	Remote Similarity	NPC213206
0.6985	Remote Similarity	NPC151237
0.6985	Remote Similarity	NPC27198
0.6985	Remote Similarity	NPC71090
0.6985	Remote Similarity	NPC261661
0.6984	Remote Similarity	NPC326447
0.6978	Remote Similarity	NPC149796
0.6972	Remote Similarity	NPC66643
0.6972	Remote Similarity	NPC266425
0.6972	Remote Similarity	NPC273984
0.697	Remote Similarity	NPC258992
0.697	Remote Similarity	NPC54507
0.697	Remote Similarity	NPC85292
0.697	Remote Similarity	NPC229147
0.697	Remote Similarity	NPC312105
0.6963	Remote Similarity	NPC212559
0.6963	Remote Similarity	NPC318357
0.6963	Remote Similarity	NPC472596
0.696	Remote Similarity	NPC12987
0.696	Remote Similarity	NPC474603
0.6957	Remote Similarity	NPC28476
0.6957	Remote Similarity	NPC133407
0.6957	Remote Similarity	NPC110131
0.6957	Remote Similarity	NPC81641
0.6953	Remote Similarity	NPC82016
0.6947	Remote Similarity	NPC161696
0.6944	Remote Similarity	NPC307682
0.694	Remote Similarity	NPC474320
0.6934	Remote Similarity	NPC320287
0.6934	Remote Similarity	NPC470887
0.6934	Remote Similarity	NPC315807
0.6934	Remote Similarity	NPC279379
0.6933	Remote Similarity	NPC115144
0.6933	Remote Similarity	NPC144863
0.6933	Remote Similarity	NPC90844
0.6933	Remote Similarity	NPC277857
0.6933	Remote Similarity	NPC95075
0.6933	Remote Similarity	NPC253883
0.6929	Remote Similarity	NPC87224
0.6929	Remote Similarity	NPC53986

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 NPC255253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	943
0.2-0.3	1043
0.3-0.4	2199
0.4-0.5	2376
0.5-0.6	1505
0.6-0.7	711
0.7-0.8	168
0.8-0.85	18
0.85-0.9	6
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6539	Approved
1.0	High Similarity	NPD6542	Approved
1.0	High Similarity	NPD6540	Phase 3
1.0	High Similarity	NPD6543	Approved
0.9746	High Similarity	NPD6541	Approved
0.9746	High Similarity	NPD6538	Approved
0.9483	High Similarity	NPD6580	Approved
0.9483	High Similarity	NPD6581	Approved
0.9402	High Similarity	NPD6830	Clinical (unspecified phase)
0.931	High Similarity	NPD3596	Phase 2
0.9016	High Similarity	NPD6583	Phase 3
0.9016	High Similarity	NPD6582	Phase 2
0.8952	High Similarity	NPD7018	Phase 2
0.8898	High Similarity	NPD2557	Approved
0.88	High Similarity	NPD6584	Phase 3
0.8547	High Similarity	NPD5451	Approved
0.8529	High Similarity	NPD6815	Approved
0.8462	Intermediate Similarity	NPD7265	Discontinued
0.845	Intermediate Similarity	NPD6179	Discontinued
0.8385	Intermediate Similarity	NPD7294	Phase 1
0.8346	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.8306	Intermediate Similarity	NPD2595	Approved
0.8306	Intermediate Similarity	NPD2594	Approved
0.824	Intermediate Similarity	NPD5846	Approved
0.824	Intermediate Similarity	NPD6516	Phase 2
0.8217	Intermediate Similarity	NPD2990	Approved
0.8217	Intermediate Similarity	NPD2987	Approved
0.816	Intermediate Similarity	NPD3444	Approved
0.816	Intermediate Similarity	NPD3443	Approved
0.816	Intermediate Similarity	NPD3445	Approved
0.8106	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD6382	Discontinued
0.8016	Intermediate Similarity	NPD3049	Approved
0.8015	Intermediate Similarity	NPD4993	Discontinued
0.8	Intermediate Similarity	NPD4098	Discontinued
0.7986	Intermediate Similarity	NPD7466	Approved
0.7971	Intermediate Similarity	NPD7037	Approved
0.797	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4188	Approved
0.7949	Intermediate Similarity	NPD4189	Approved
0.7941	Intermediate Similarity	NPD7119	Phase 2
0.7937	Intermediate Similarity	NPD2486	Discontinued
0.7926	Intermediate Similarity	NPD4618	Approved
0.7926	Intermediate Similarity	NPD4622	Approved
0.7917	Intermediate Similarity	NPD5374	Approved
0.7917	Intermediate Similarity	NPD5373	Approved
0.7863	Intermediate Similarity	NPD2555	Approved
0.7863	Intermediate Similarity	NPD2550	Approved
0.7863	Intermediate Similarity	NPD2552	Approved
0.7863	Intermediate Similarity	NPD2549	Approved
0.7863	Intermediate Similarity	NPD2553	Approved
0.7863	Intermediate Similarity	NPD2558	Approved
0.7846	Intermediate Similarity	NPD2429	Approved
0.7846	Intermediate Similarity	NPD2428	Approved
0.7823	Intermediate Similarity	NPD2988	Approved
0.7823	Intermediate Similarity	NPD2991	Approved
0.782	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD7213	Phase 3
0.7817	Intermediate Similarity	NPD7212	Phase 2
0.7812	Intermediate Similarity	NPD2554	Approved
0.7812	Intermediate Similarity	NPD2556	Approved
0.781	Intermediate Similarity	NPD5688	Approved
0.781	Intermediate Similarity	NPD5689	Approved
0.7778	Intermediate Similarity	NPD3532	Approved
0.7778	Intermediate Similarity	NPD3530	Approved
0.7778	Intermediate Similarity	NPD3531	Approved
0.777	Intermediate Similarity	NPD7030	Discontinued
0.7762	Intermediate Similarity	NPD7447	Phase 1
0.7752	Intermediate Similarity	NPD3294	Phase 2
0.7742	Intermediate Similarity	NPD5535	Approved
0.7737	Intermediate Similarity	NPD3054	Approved
0.7737	Intermediate Similarity	NPD3052	Approved
0.771	Intermediate Similarity	NPD3685	Discontinued
0.7704	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2667	Approved
0.7674	Intermediate Similarity	NPD2668	Approved
0.7667	Intermediate Similarity	NPD3048	Approved
0.7667	Intermediate Similarity	NPD3046	Approved
0.7667	Intermediate Similarity	NPD3047	Approved
0.7656	Intermediate Similarity	NPD4016	Approved
0.7647	Intermediate Similarity	NPD4474	Approved
0.7647	Intermediate Similarity	NPD4475	Approved
0.763	Intermediate Similarity	NPD5163	Phase 2
0.763	Intermediate Similarity	NPD5746	Approved
0.7626	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1819	Approved
0.7594	Intermediate Similarity	NPD1818	Approved
0.7594	Intermediate Similarity	NPD1820	Approved
0.7594	Intermediate Similarity	NPD1817	Approved
0.7591	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD2671	Approved
0.7581	Intermediate Similarity	NPD2673	Approved
0.7561	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD2200	Suspended
0.7551	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2551	Approved
0.7541	Intermediate Similarity	NPD2559	Approved
0.754	Intermediate Similarity	NPD594	Approved
0.754	Intermediate Similarity	NPD592	Approved
0.7518	Intermediate Similarity	NPD2376	Approved
0.7518	Intermediate Similarity	NPD2378	Approved
0.7518	Intermediate Similarity	NPD7477	Discontinued
0.7518	Intermediate Similarity	NPD5745	Approved
0.7518	Intermediate Similarity	NPD2377	Approved
0.7518	Intermediate Similarity	NPD5085	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3165	Approved
0.75	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3167	Approved
0.75	Intermediate Similarity	NPD3166	Approved
0.75	Intermediate Similarity	NPD3164	Approved
0.7481	Intermediate Similarity	NPD2237	Approved
0.7465	Intermediate Similarity	NPD2897	Discontinued
0.746	Intermediate Similarity	NPD821	Approved
0.7447	Intermediate Similarity	NPD6032	Approved
0.7405	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3526	Approved
0.7398	Intermediate Similarity	NPD3524	Approved
0.7372	Intermediate Similarity	NPD3180	Approved
0.7372	Intermediate Similarity	NPD3179	Approved
0.7338	Intermediate Similarity	NPD3110	Approved
0.7338	Intermediate Similarity	NPD3140	Approved
0.7338	Intermediate Similarity	NPD6225	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3109	Approved
0.7338	Intermediate Similarity	NPD3142	Approved
0.7333	Intermediate Similarity	NPD1794	Approved
0.7324	Intermediate Similarity	NPD4476	Approved
0.7324	Intermediate Similarity	NPD4477	Approved
0.7323	Intermediate Similarity	NPD7843	Approved
0.7319	Intermediate Similarity	NPD5718	Phase 2
0.7292	Intermediate Similarity	NPD4162	Approved
0.7292	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7019	Approved
0.7279	Intermediate Similarity	NPD7020	Approved
0.7279	Intermediate Similarity	NPD7905	Discontinued
0.7266	Intermediate Similarity	NPD3163	Approved
0.7266	Intermediate Similarity	NPD3162	Approved
0.7266	Intermediate Similarity	NPD1423	Approved
0.7254	Intermediate Similarity	NPD2156	Approved
0.7254	Intermediate Similarity	NPD2154	Approved
0.7254	Intermediate Similarity	NPD2155	Approved
0.7252	Intermediate Similarity	NPD7042	Phase 3
0.7241	Intermediate Similarity	NPD6748	Discontinued
0.7239	Intermediate Similarity	NPD2233	Approved
0.7239	Intermediate Similarity	NPD2230	Approved
0.7239	Intermediate Similarity	NPD2232	Approved
0.7237	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2986	Phase 2
0.7234	Intermediate Similarity	NPD2989	Phase 2
0.7231	Intermediate Similarity	NPD5500	Discontinued
0.7222	Intermediate Similarity	NPD2170	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1725	Approved
0.7194	Intermediate Similarity	NPD1336	Approved
0.7192	Intermediate Similarity	NPD5241	Discontinued
0.7188	Intermediate Similarity	NPD2496	Approved
0.7188	Intermediate Similarity	NPD2497	Approved
0.7185	Intermediate Similarity	NPD1669	Approved
0.7185	Intermediate Similarity	NPD5327	Phase 3
0.7185	Intermediate Similarity	NPD4659	Approved
0.7183	Intermediate Similarity	NPD4538	Approved
0.7183	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4536	Approved
0.7181	Intermediate Similarity	NPD7131	Phase 3
0.7181	Intermediate Similarity	NPD7427	Discontinued
0.7174	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD5061	Approved
0.7172	Intermediate Similarity	NPD4236	Phase 3
0.7172	Intermediate Similarity	NPD4237	Approved
0.7172	Intermediate Similarity	NPD5289	Phase 2
0.7172	Intermediate Similarity	NPD2460	Phase 3
0.7172	Intermediate Similarity	NPD5062	Approved
0.7172	Intermediate Similarity	NPD2458	Approved
0.7172	Intermediate Similarity	NPD2459	Approved
0.7171	Intermediate Similarity	NPD6280	Approved
0.7171	Intermediate Similarity	NPD6279	Approved
0.7154	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7143	Intermediate Similarity	NPD4594	Approved
0.7143	Intermediate Similarity	NPD4593	Approved
0.7133	Intermediate Similarity	NPD2661	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6380	Phase 1
0.7132	Intermediate Similarity	NPD5283	Phase 1
0.7124	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1182	Approved
0.712	Intermediate Similarity	NPD811	Approved
0.712	Intermediate Similarity	NPD812	Approved
0.712	Intermediate Similarity	NPD810	Approved
0.712	Intermediate Similarity	NPD968	Approved
0.7114	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2235	Phase 2
0.7111	Intermediate Similarity	NPD2231	Phase 2

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