NPASS Compound

Structure

CID204303 OpenBabel06191715592D 28 32 0 0 1 0 0 0 0 0999 V2000 2.4743 -2.4436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0455 -1.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5142 -1.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -1.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3533 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1918 -0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1920 -3.3882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 -2.9041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6770 -1.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8378 -1.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5148 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8385 -1.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5149 -1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8379 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1918 -1.4518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0304 -2.9040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6769 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8385 -0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5379 -1.0567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 -1.9359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0303 -1.9358 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6768 1.0001 0.0000 Cl 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 5.9096 -3.4115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5530 -1.0566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0302 -0.1775 0.0000 O 0 0 0 0 0 0 0 0 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 12 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 17 22 1 1 0 0 0 17 23 1 0 0 0 0 18 23 1 1 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 1 1 1 0 0 0 23 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	397.14
Volume:	397.705
LogP:	4.883
LogD:	3.757
LogS:	-4.562
# Rotatable Bonds:	1
TPSA:	73.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	3.974
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.94
MDCK Permeability:	1.978774344024714e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.617

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	96.9165267944336%
Volume Distribution (VD):	0.44
Pgp-substrate:	1.7681864500045776%

ADMET: Metabolism

CYP1A2-inhibitor:	0.765
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.474
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.509
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.175
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	5.054
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.398
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.89
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.358
Carcinogencity:	0.446
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC204303

Natural Product ID:	NPC204303
*Common Name:**	BICHPFOJNXXLDH-FKKSXTGDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BICHPFOJNXXLDH-FKKSXTGDSA-N
Standard InCHI:	InChI=1S/C23H24ClNO3/c1-22-10-9-18(26)23(2,21(27)28)17(22)8-7-13-15(22)11-14-12-5-3-4-6-16(12)25-20(14)19(13)24/h3-6,11,17-18,25-26H,7-10H2,1-2H3,(H,27,28)/t17-,18+,22-,23+/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@H]([C@]1(C)C(=O)O)CCc1c2cc2c(c1Cl)[nH]c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3786027
PubChem CID:	70676037
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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
NPO40855	Halophilic actinomycete	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26698879]

☑ 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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	162080.0	nM	PMID[505323]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	12760.0	nM	PMID[505323]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	12.89	n.a.	PMID[505323]

☑ 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 NPC204303 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	307
0.1-0.2	1641
0.2-0.3	6863
0.3-0.4	23404
0.4-0.5	6736
0.5-0.6	2580
0.6-0.7	1049
0.7-0.8	109
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9198	High Similarity	NPC181502
0.9198	High Similarity	NPC85066
0.801	Intermediate Similarity	NPC473747
0.7931	Intermediate Similarity	NPC475151
0.7826	Intermediate Similarity	NPC18661
0.7778	Intermediate Similarity	NPC99428
0.7762	Intermediate Similarity	NPC475165
0.7756	Intermediate Similarity	NPC81654
0.7756	Intermediate Similarity	NPC313985
0.7756	Intermediate Similarity	NPC249150
0.7756	Intermediate Similarity	NPC49196
0.7756	Intermediate Similarity	NPC195461
0.7756	Intermediate Similarity	NPC79129
0.7752	Intermediate Similarity	NPC79107
0.7752	Intermediate Similarity	NPC475424
0.775	Intermediate Similarity	NPC206967
0.7749	Intermediate Similarity	NPC154293
0.7745	Intermediate Similarity	NPC50503
0.7725	Intermediate Similarity	NPC250129
0.7629	Intermediate Similarity	NPC97525
0.7594	Intermediate Similarity	NPC234999
0.7591	Intermediate Similarity	NPC112547
0.7576	Intermediate Similarity	NPC302191
0.7547	Intermediate Similarity	NPC284102
0.7525	Intermediate Similarity	NPC198339
0.75	Intermediate Similarity	NPC61637
0.7488	Intermediate Similarity	NPC473547
0.7488	Intermediate Similarity	NPC187456
0.7475	Intermediate Similarity	NPC213468
0.7475	Intermediate Similarity	NPC119700
0.7454	Intermediate Similarity	NPC97388
0.7442	Intermediate Similarity	NPC475778
0.7437	Intermediate Similarity	NPC300688
0.7413	Intermediate Similarity	NPC165201
0.74	Intermediate Similarity	NPC192270
0.7398	Intermediate Similarity	NPC126492
0.7373	Intermediate Similarity	NPC160527
0.7373	Intermediate Similarity	NPC473650
0.7368	Intermediate Similarity	NPC476175
0.7364	Intermediate Similarity	NPC61813
0.7363	Intermediate Similarity	NPC19679
0.7333	Intermediate Similarity	NPC471634
0.7333	Intermediate Similarity	NPC473806
0.7321	Intermediate Similarity	NPC52557
0.7308	Intermediate Similarity	NPC205403
0.7268	Intermediate Similarity	NPC175474
0.7264	Intermediate Similarity	NPC162730
0.7264	Intermediate Similarity	NPC123019
0.7264	Intermediate Similarity	NPC474116
0.7257	Intermediate Similarity	NPC472844
0.725	Intermediate Similarity	NPC151939
0.7227	Intermediate Similarity	NPC96131
0.7225	Intermediate Similarity	NPC231342
0.7206	Intermediate Similarity	NPC476319
0.7186	Intermediate Similarity	NPC34508
0.7184	Intermediate Similarity	NPC34271
0.7172	Intermediate Similarity	NPC280548
0.7164	Intermediate Similarity	NPC293472
0.7162	Intermediate Similarity	NPC475476
0.7162	Intermediate Similarity	NPC242446
0.7149	Intermediate Similarity	NPC282033
0.7136	Intermediate Similarity	NPC471284
0.7136	Intermediate Similarity	NPC6982
0.7129	Intermediate Similarity	NPC6093
0.7123	Intermediate Similarity	NPC235900
0.7114	Intermediate Similarity	NPC288785
0.7095	Intermediate Similarity	NPC472843
0.707	Intermediate Similarity	NPC477135
0.7067	Intermediate Similarity	NPC329858
0.7044	Intermediate Similarity	NPC270009
0.7035	Intermediate Similarity	NPC201700
0.7027	Intermediate Similarity	NPC204491
0.7027	Intermediate Similarity	NPC203614
0.702	Intermediate Similarity	NPC470508
0.7005	Intermediate Similarity	NPC16667
0.7004	Intermediate Similarity	NPC235885
0.7	Intermediate Similarity	NPC55493
0.7	Intermediate Similarity	NPC9894
0.6991	Remote Similarity	NPC98715
0.6986	Remote Similarity	NPC95783
0.6981	Remote Similarity	NPC11445
0.6974	Remote Similarity	NPC184476
0.6972	Remote Similarity	NPC477065
0.6963	Remote Similarity	NPC32200
0.6963	Remote Similarity	NPC241024
0.6959	Remote Similarity	NPC200743
0.6949	Remote Similarity	NPC470843
0.6949	Remote Similarity	NPC94541
0.6944	Remote Similarity	NPC476874
0.6941	Remote Similarity	NPC258062
0.6941	Remote Similarity	NPC127677
0.6934	Remote Similarity	NPC195239
0.6934	Remote Similarity	NPC157828
0.6923	Remote Similarity	NPC160381
0.6915	Remote Similarity	NPC312092
0.6905	Remote Similarity	NPC314333
0.6898	Remote Similarity	NPC300183
0.6897	Remote Similarity	NPC329688
0.6897	Remote Similarity	NPC189812
0.6895	Remote Similarity	NPC225821
0.6895	Remote Similarity	NPC46225
0.6884	Remote Similarity	NPC162799
0.6884	Remote Similarity	NPC472587
0.6878	Remote Similarity	NPC303951
0.6869	Remote Similarity	NPC229332
0.6866	Remote Similarity	NPC78020
0.6857	Remote Similarity	NPC128751
0.6857	Remote Similarity	NPC246700
0.6853	Remote Similarity	NPC76982
0.6852	Remote Similarity	NPC214428
0.685	Remote Similarity	NPC71132
0.6847	Remote Similarity	NPC23294
0.6844	Remote Similarity	NPC293151
0.6842	Remote Similarity	NPC315555
0.6842	Remote Similarity	NPC1203
0.6839	Remote Similarity	NPC477134
0.6837	Remote Similarity	NPC477044
0.6837	Remote Similarity	NPC477041
0.6835	Remote Similarity	NPC476115
0.6833	Remote Similarity	NPC271862
0.6825	Remote Similarity	NPC106833
0.6825	Remote Similarity	NPC469497
0.6822	Remote Similarity	NPC188239
0.6818	Remote Similarity	NPC474905
0.6818	Remote Similarity	NPC67056
0.6818	Remote Similarity	NPC323927
0.6816	Remote Similarity	NPC151976
0.6816	Remote Similarity	NPC87856
0.6812	Remote Similarity	NPC51388
0.6812	Remote Similarity	NPC147446
0.6806	Remote Similarity	NPC477045
0.6804	Remote Similarity	NPC124005
0.6802	Remote Similarity	NPC285469
0.68	Remote Similarity	NPC132211
0.68	Remote Similarity	NPC3207
0.6798	Remote Similarity	NPC2395
0.6796	Remote Similarity	NPC219336
0.6791	Remote Similarity	NPC153042
0.6786	Remote Similarity	NPC267965
0.6784	Remote Similarity	NPC473320
0.6783	Remote Similarity	NPC245756
0.6783	Remote Similarity	NPC141428
0.6781	Remote Similarity	NPC474701
0.678	Remote Similarity	NPC267885
0.6779	Remote Similarity	NPC472108
0.6779	Remote Similarity	NPC139291
0.6777	Remote Similarity	NPC46413
0.6777	Remote Similarity	NPC321708
0.6769	Remote Similarity	NPC33421
0.6762	Remote Similarity	NPC235684
0.6761	Remote Similarity	NPC47190
0.6759	Remote Similarity	NPC102008
0.6757	Remote Similarity	NPC469743
0.6753	Remote Similarity	NPC267926
0.6751	Remote Similarity	NPC38736
0.6751	Remote Similarity	NPC207726
0.6751	Remote Similarity	NPC470507
0.6748	Remote Similarity	NPC183662
0.6748	Remote Similarity	NPC15573
0.6748	Remote Similarity	NPC68354
0.6748	Remote Similarity	NPC217372
0.6739	Remote Similarity	NPC266192
0.6735	Remote Similarity	NPC478080
0.6732	Remote Similarity	NPC149155
0.6732	Remote Similarity	NPC472586
0.6732	Remote Similarity	NPC275305
0.6732	Remote Similarity	NPC110500
0.6732	Remote Similarity	NPC203468
0.6732	Remote Similarity	NPC37423
0.6726	Remote Similarity	NPC475422
0.6726	Remote Similarity	NPC330009
0.6726	Remote Similarity	NPC469928
0.6725	Remote Similarity	NPC280799
0.6724	Remote Similarity	NPC57690
0.6723	Remote Similarity	NPC323198
0.6719	Remote Similarity	NPC472845
0.6715	Remote Similarity	NPC126709
0.6715	Remote Similarity	NPC55772
0.6715	Remote Similarity	NPC176199
0.6715	Remote Similarity	NPC472443
0.6715	Remote Similarity	NPC215795
0.6715	Remote Similarity	NPC248041
0.6714	Remote Similarity	NPC473189
0.6712	Remote Similarity	NPC86834
0.6712	Remote Similarity	NPC193761
0.6712	Remote Similarity	NPC87755
0.6712	Remote Similarity	NPC39679
0.6712	Remote Similarity	NPC210828
0.6711	Remote Similarity	NPC31700
0.6698	Remote Similarity	NPC63199
0.6698	Remote Similarity	NPC196251
0.6698	Remote Similarity	NPC102338
0.6698	Remote Similarity	NPC111602
0.6697	Remote Similarity	NPC277350
0.6696	Remote Similarity	NPC469312
0.6696	Remote Similarity	NPC41318
0.6683	Remote Similarity	NPC469896
0.6683	Remote Similarity	NPC472123
0.6682	Remote Similarity	NPC478158
0.6682	Remote Similarity	NPC67551

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 NPC204303 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	616
0.2-0.3	744
0.3-0.4	2204
0.4-0.5	3267
0.5-0.6	1719
0.6-0.7	359
0.7-0.8	11
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
0.7879	Intermediate Similarity	NPD1534	Approved
0.7756	Intermediate Similarity	NPD4601	Approved
0.7756	Intermediate Similarity	NPD4600	Approved
0.7711	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5003	Discontinued
0.7268	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6846	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7957	Phase 1
0.707	Intermediate Similarity	NPD2920	Discontinued
0.7059	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5021	Discontinued
0.702	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2565	Phase 2
0.6986	Remote Similarity	NPD2564	Approved
0.6965	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD43	Approved
0.6931	Remote Similarity	NPD6182	Approved
0.6931	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5897	Approved
0.6927	Remote Similarity	NPD5899	Approved
0.6927	Remote Similarity	NPD5898	Approved
0.6905	Remote Similarity	NPD4499	Approved
0.6898	Remote Similarity	NPD7931	Approved
0.6898	Remote Similarity	NPD7934	Discovery
0.6898	Remote Similarity	NPD7933	Approved
0.6898	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8431	Approved
0.6884	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5471	Phase 3
0.686	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7772	Phase 3
0.6804	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4076	Approved
0.6796	Remote Similarity	NPD4079	Approved
0.6782	Remote Similarity	NPD2844	Phase 3
0.678	Remote Similarity	NPD5501	Discontinued
0.678	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7233	Approved
0.6777	Remote Similarity	NPD7234	Approved
0.6776	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5254	Discontinued
0.677	Remote Similarity	NPD7185	Discontinued
0.6759	Remote Similarity	NPD7777	Approved
0.6759	Remote Similarity	NPD53	Approved
0.6759	Remote Similarity	NPD7778	Approved
0.6748	Remote Similarity	NPD3506	Approved
0.6748	Remote Similarity	NPD3505	Approved
0.6742	Remote Similarity	NPD5429	Discontinued
0.6741	Remote Similarity	NPD7455	Approved
0.6741	Remote Similarity	NPD7454	Approved
0.6739	Remote Similarity	NPD7548	Discontinued
0.6732	Remote Similarity	NPD482	Approved
0.6727	Remote Similarity	NPD5901	Discontinued
0.6726	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7187	Phase 2
0.6711	Remote Similarity	NPD8094	Discontinued
0.6699	Remote Similarity	NPD2092	Phase 2
0.6699	Remote Similarity	NPD2094	Phase 2
0.6699	Remote Similarity	NPD2095	Phase 2
0.6697	Remote Similarity	NPD6479	Discontinued
0.6696	Remote Similarity	NPD6995	Phase 1
0.6695	Remote Similarity	NPD7576	Discontinued
0.6682	Remote Similarity	NPD6176	Phase 1
0.6667	Remote Similarity	NPD1326	Approved
0.6667	Remote Similarity	NPD1325	Approved
0.6667	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8093	Discontinued
0.6667	Remote Similarity	NPD2096	Phase 2
0.6667	Remote Similarity	NPD2091	Phase 2
0.6652	Remote Similarity	NPD6987	Phase 1
0.665	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD8386	Phase 2
0.6622	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4501	Approved
0.6621	Remote Similarity	NPD4500	Approved
0.6608	Remote Similarity	NPD7707	Approved
0.6603	Remote Similarity	NPD5473	Discontinued
0.6599	Remote Similarity	NPD4463	Approved
0.6599	Remote Similarity	NPD4462	Approved
0.6594	Remote Similarity	NPD7878	Phase 2
0.6591	Remote Similarity	NPD4511	Phase 1
0.6588	Remote Similarity	NPD6178	Phase 3
0.6583	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8238	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6664	Approved
0.6552	Remote Similarity	NPD3323	Discontinued
0.6549	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7944	Discontinued
0.654	Remote Similarity	NPD3318	Approved
0.654	Remote Similarity	NPD3319	Phase 1
0.654	Remote Similarity	NPD3320	Approved
0.6538	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1553	Approved
0.653	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD750	Phase 2
0.6518	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2144	Approved
0.6493	Remote Similarity	NPD3038	Discontinued
0.6479	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7470	Discontinued
0.6473	Remote Similarity	NPD7010	Phase 3
0.6459	Remote Similarity	NPD4075	Phase 2
0.6457	Remote Similarity	NPD8072	Approved
0.6456	Remote Similarity	NPD4638	Approved
0.6456	Remote Similarity	NPD4640	Approved
0.6456	Remote Similarity	NPD4639	Approved
0.6455	Remote Similarity	NPD2727	Phase 2
0.6445	Remote Similarity	NPD6595	Phase 3
0.6445	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7953	Approved
0.6444	Remote Similarity	NPD7791	Approved
0.6444	Remote Similarity	NPD7790	Approved
0.6444	Remote Similarity	NPD7950	Approved
0.6444	Remote Similarity	NPD7952	Approved
0.6444	Remote Similarity	NPD7789	Approved
0.6444	Remote Similarity	NPD7951	Approved
0.6442	Remote Similarity	NPD7418	Discontinued
0.644	Remote Similarity	NPD4880	Discontinued
0.6435	Remote Similarity	NPD6281	Approved
0.6432	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5498	Phase 2
0.6429	Remote Similarity	NPD7688	Phase 1
0.6429	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5426	Phase 3
0.6429	Remote Similarity	NPD8114	Approved
0.6429	Remote Similarity	NPD8115	Approved
0.6419	Remote Similarity	NPD3961	Discontinued
0.6419	Remote Similarity	NPD4948	Discontinued
0.6416	Remote Similarity	NPD2916	Discontinued
0.6416	Remote Similarity	NPD7191	Phase 2
0.641	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4918	Discontinued
0.6406	Remote Similarity	NPD5913	Phase 3
0.6406	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1587	Approved
0.6397	Remote Similarity	NPD7658	Phase 2
0.6395	Remote Similarity	NPD3280	Approved
0.6393	Remote Similarity	NPD5803	Suspended
0.6393	Remote Similarity	NPD4602	Approved
0.6391	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7824	Approved
0.6385	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3222	Phase 2
0.6382	Remote Similarity	NPD5807	Phase 2
0.6379	Remote Similarity	NPD7395	Discontinued
0.6377	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD1262	Discovery
0.6372	Remote Similarity	NPD6217	Discontinued
0.6372	Remote Similarity	NPD4346	Phase 3
0.6372	Remote Similarity	NPD5809	Phase 3
0.6368	Remote Similarity	NPD6515	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6514	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5512	Phase 3
0.6364	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2306	Approved
0.6352	Remote Similarity	NPD3258	Approved
0.6351	Remote Similarity	NPD4181	Approved
0.6351	Remote Similarity	NPD7865	Approved
0.6346	Remote Similarity	NPD7474	Suspended
0.6346	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6376	Discontinued
0.6343	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8073	Approved
0.6336	Remote Similarity	NPD5164	Discontinued
0.6333	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD5936	Approved
0.6332	Remote Similarity	NPD5939	Approved
0.6323	Remote Similarity	NPD2305	Discontinued
0.6318	Remote Similarity	NPD8364	Approved
0.6318	Remote Similarity	NPD8363	Approved
0.6318	Remote Similarity	NPD7618	Phase 3
0.6318	Remote Similarity	NPD7619	Phase 3
0.6316	Remote Similarity	NPD5835	Phase 3
0.6316	Remote Similarity	NPD5834	Phase 3
0.631	Remote Similarity	NPD8244	Phase 2
0.6304	Remote Similarity	NPD7069	Discontinued
0.6304	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7731	Approved
0.6303	Remote Similarity	NPD7730	Approved
0.6303	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8322	Phase 2
0.6296	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8358	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