NPASS Compound

Structure

CID249150 OpenBabel06191716052D 26 30 0 0 1 0 0 0 0 0999 V2000 -0.1219 2.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5162 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -1.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6775 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1941 1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1943 2.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 -1.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5163 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3551 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3554 0.9675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8388 -1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 -1.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5170 1.4519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8386 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6780 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3559 2.9040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5172 2.4201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8389 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6376 2.9283 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 2.5165 -0.4847 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.3562 3.9199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6379 3.9442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 2.4206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 13 2 0 0 0 0 5 16 2 0 0 0 0 6 7 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 6 1 6 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 15 10 1 6 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 21 1 1 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.19
Volume:	364.172
LogP:	2.785
LogD:	2.762
LogS:	-2.77
# Rotatable Bonds:	2
TPSA:	65.56
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	3.875
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.123
MDCK Permeability:	2.384961953794118e-05
Pgp-inhibitor:	0.344
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.341
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.695
Plasma Protein Binding (PPB):	62.36962890625%
Volume Distribution (VD):	1.82
Pgp-substrate:	37.83748245239258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.273
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.804

ADMET: Excretion

Clearance (CL):	10.943
Half-life (T1/2):	0.388

ADMET: Toxicity

hERG Blockers:	0.603
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.433
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.732
Carcinogencity:	0.736
Eye Corrosion:	0.011
Eye Irritation:	0.058
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC249150

Natural Product ID:	NPC249150
*Common Name:**	Methyl (1S,15S,18S,19R,20S)-18-Hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-Carboxylate
IUPAC Name:	methyl (1S,15S,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Synonyms:
Standard InCHIKey:	BLGXFZZNTVWLAY-FJDMERLMSA-N
Standard InCHI:	InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17+,18+,19-/m1/s1
SMILES:	COC(=O)[C@H]1[C@@H](O)CC[C@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1526082
PubChem CID:	120716
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001786] Yohimbine 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
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Potency	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	31622.8	nM	PMID[473010]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[473011]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[473010]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[473012]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[473011]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[473010]

☑ 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 NPC249150 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	245
0.1-0.2	1263
0.2-0.3	5188
0.3-0.4	22056
0.4-0.5	8499
0.5-0.6	2819
0.6-0.7	1891
0.7-0.8	613
0.8-0.85	88
0.85-0.9	18
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC81654
1.0	High Similarity	NPC79129
1.0	High Similarity	NPC49196
1.0	High Similarity	NPC313985
1.0	High Similarity	NPC195461
0.9887	High Similarity	NPC50503
0.9435	High Similarity	NPC175474
0.9235	High Similarity	NPC52557
0.8696	High Similarity	NPC111602
0.8696	High Similarity	NPC63199
0.8696	High Similarity	NPC102338
0.8696	High Similarity	NPC196251
0.8649	High Similarity	NPC472112
0.8626	High Similarity	NPC472108
0.8626	High Similarity	NPC139291
0.8556	High Similarity	NPC472113
0.8541	High Similarity	NPC472323
0.8534	High Similarity	NPC312870
0.8534	High Similarity	NPC128265
0.8534	High Similarity	NPC199851
0.8534	High Similarity	NPC294909
0.8534	High Similarity	NPC254240
0.852	High Similarity	NPC234999
0.8516	High Similarity	NPC15840
0.8462	Intermediate Similarity	NPC219336
0.8446	Intermediate Similarity	NPC162730
0.8444	Intermediate Similarity	NPC472123
0.8432	Intermediate Similarity	NPC79062
0.8432	Intermediate Similarity	NPC472107
0.8415	Intermediate Similarity	NPC469896
0.8407	Intermediate Similarity	NPC183662
0.8407	Intermediate Similarity	NPC217372
0.8407	Intermediate Similarity	NPC15573
0.8368	Intermediate Similarity	NPC85066
0.8368	Intermediate Similarity	NPC181502
0.8351	Intermediate Similarity	NPC474116
0.8342	Intermediate Similarity	NPC475778
0.8325	Intermediate Similarity	NPC245916
0.8324	Intermediate Similarity	NPC472110
0.8324	Intermediate Similarity	NPC472109
0.828	Intermediate Similarity	NPC472119
0.8278	Intermediate Similarity	NPC317430
0.8276	Intermediate Similarity	NPC52254
0.8272	Intermediate Similarity	NPC19692
0.8272	Intermediate Similarity	NPC220151
0.8254	Intermediate Similarity	NPC329858
0.8226	Intermediate Similarity	NPC143533
0.8212	Intermediate Similarity	NPC271797
0.8212	Intermediate Similarity	NPC21174
0.8197	Intermediate Similarity	NPC329688
0.8197	Intermediate Similarity	NPC189812
0.8182	Intermediate Similarity	NPC258480
0.8168	Intermediate Similarity	NPC55493
0.8158	Intermediate Similarity	NPC469501
0.8158	Intermediate Similarity	NPC314333
0.8158	Intermediate Similarity	NPC469470
0.8152	Intermediate Similarity	NPC24594
0.8152	Intermediate Similarity	NPC472122
0.8137	Intermediate Similarity	NPC82070
0.8128	Intermediate Similarity	NPC476114
0.8128	Intermediate Similarity	NPC19679
0.8103	Intermediate Similarity	NPC241024
0.8095	Intermediate Similarity	NPC66210
0.8083	Intermediate Similarity	NPC289299
0.8083	Intermediate Similarity	NPC57994
0.8049	Intermediate Similarity	NPC281049
0.8049	Intermediate Similarity	NPC174788
0.8048	Intermediate Similarity	NPC33949
0.804	Intermediate Similarity	NPC18661
0.8032	Intermediate Similarity	NPC472104
0.8031	Intermediate Similarity	NPC472295
0.8031	Intermediate Similarity	NPC81802
0.8031	Intermediate Similarity	NPC472210
0.8031	Intermediate Similarity	NPC247735
0.8031	Intermediate Similarity	NPC269886
0.8029	Intermediate Similarity	NPC475271
0.8021	Intermediate Similarity	NPC472105
0.8021	Intermediate Similarity	NPC187827
0.8021	Intermediate Similarity	NPC472097
0.8	Intermediate Similarity	NPC478077
0.7979	Intermediate Similarity	NPC113626
0.7968	Intermediate Similarity	NPC213468
0.7941	Intermediate Similarity	NPC221100
0.7941	Intermediate Similarity	NPC234078
0.7921	Intermediate Similarity	NPC469743
0.7921	Intermediate Similarity	NPC478158
0.7914	Intermediate Similarity	NPC326575
0.791	Intermediate Similarity	NPC477065
0.7906	Intermediate Similarity	NPC235684
0.7906	Intermediate Similarity	NPC62749
0.7889	Intermediate Similarity	NPC476874
0.7879	Intermediate Similarity	NPC214428
0.7876	Intermediate Similarity	NPC95783
0.7864	Intermediate Similarity	NPC330009
0.7864	Intermediate Similarity	NPC148183
0.7864	Intermediate Similarity	NPC152768
0.7864	Intermediate Similarity	NPC469928
0.7861	Intermediate Similarity	NPC267885
0.7857	Intermediate Similarity	NPC472116
0.7849	Intermediate Similarity	NPC161861
0.7831	Intermediate Similarity	NPC91179
0.782	Intermediate Similarity	NPC21638
0.7819	Intermediate Similarity	NPC234987
0.7816	Intermediate Similarity	NPC478157
0.7812	Intermediate Similarity	NPC315555
0.7812	Intermediate Similarity	NPC99428
0.7807	Intermediate Similarity	NPC110500
0.7807	Intermediate Similarity	NPC149155
0.7807	Intermediate Similarity	NPC203468
0.7789	Intermediate Similarity	NPC249040
0.7784	Intermediate Similarity	NPC206967
0.7784	Intermediate Similarity	NPC78020
0.7784	Intermediate Similarity	NPC154293
0.7778	Intermediate Similarity	NPC126709
0.7778	Intermediate Similarity	NPC248041
0.7778	Intermediate Similarity	NPC133261
0.7772	Intermediate Similarity	NPC277350
0.7761	Intermediate Similarity	NPC476098
0.7756	Intermediate Similarity	NPC204303
0.7737	Intermediate Similarity	NPC300688
0.7736	Intermediate Similarity	NPC235885
0.7732	Intermediate Similarity	NPC321708
0.7725	Intermediate Similarity	NPC14113
0.7725	Intermediate Similarity	NPC145885
0.7725	Intermediate Similarity	NPC84827
0.7723	Intermediate Similarity	NPC185742
0.7723	Intermediate Similarity	NPC475847
0.7707	Intermediate Similarity	NPC475422
0.7704	Intermediate Similarity	NPC472292
0.7696	Intermediate Similarity	NPC87755
0.7692	Intermediate Similarity	NPC203614
0.7692	Intermediate Similarity	NPC204491
0.7684	Intermediate Similarity	NPC55772
0.7684	Intermediate Similarity	NPC283219
0.7681	Intermediate Similarity	NPC54744
0.768	Intermediate Similarity	NPC119700
0.7677	Intermediate Similarity	NPC231342
0.7673	Intermediate Similarity	NPC165599
0.766	Intermediate Similarity	NPC97525
0.7659	Intermediate Similarity	NPC162860
0.7653	Intermediate Similarity	NPC243716
0.765	Intermediate Similarity	NPC473105
0.7644	Intermediate Similarity	NPC313640
0.7637	Intermediate Similarity	NPC285469
0.7633	Intermediate Similarity	NPC75634
0.7632	Intermediate Similarity	NPC111275
0.7632	Intermediate Similarity	NPC151939
0.763	Intermediate Similarity	NPC472099
0.7617	Intermediate Similarity	NPC165201
0.7617	Intermediate Similarity	NPC472294
0.7609	Intermediate Similarity	NPC81229
0.7609	Intermediate Similarity	NPC255229
0.7604	Intermediate Similarity	NPC475720
0.7604	Intermediate Similarity	NPC302191
0.7604	Intermediate Similarity	NPC71037
0.7604	Intermediate Similarity	NPC474192
0.7598	Intermediate Similarity	NPC238457
0.7596	Intermediate Similarity	NPC472291
0.7588	Intermediate Similarity	NPC472293
0.7586	Intermediate Similarity	NPC476115
0.7581	Intermediate Similarity	NPC470508
0.7574	Intermediate Similarity	NPC475506
0.7568	Intermediate Similarity	NPC16667
0.7562	Intermediate Similarity	NPC472297
0.7562	Intermediate Similarity	NPC472296
0.7561	Intermediate Similarity	NPC474905
0.7561	Intermediate Similarity	NPC54420
0.7558	Intermediate Similarity	NPC14288
0.7552	Intermediate Similarity	NPC198339
0.7538	Intermediate Similarity	NPC474121
0.7537	Intermediate Similarity	NPC193761
0.7537	Intermediate Similarity	NPC155143
0.7536	Intermediate Similarity	NPC96321
0.7536	Intermediate Similarity	NPC473041
0.7526	Intermediate Similarity	NPC228835
0.7523	Intermediate Similarity	NPC64216
0.7522	Intermediate Similarity	NPC284685
0.7512	Intermediate Similarity	NPC477175
0.7512	Intermediate Similarity	NPC470730
0.7512	Intermediate Similarity	NPC102008
0.7512	Intermediate Similarity	NPC306376
0.7512	Intermediate Similarity	NPC2395
0.7512	Intermediate Similarity	NPC322135
0.7511	Intermediate Similarity	NPC470784
0.75	Intermediate Similarity	NPC11445
0.75	Intermediate Similarity	NPC201700
0.75	Intermediate Similarity	NPC261251
0.75	Intermediate Similarity	NPC98715
0.7489	Intermediate Similarity	NPC191489
0.7488	Intermediate Similarity	NPC271862
0.7488	Intermediate Similarity	NPC305984
0.7488	Intermediate Similarity	NPC477548
0.7488	Intermediate Similarity	NPC312645
0.7488	Intermediate Similarity	NPC300183
0.7486	Intermediate Similarity	NPC207726
0.7477	Intermediate Similarity	NPC475816
0.7477	Intermediate Similarity	NPC475969
0.7477	Intermediate Similarity	NPC475859
0.7476	Intermediate Similarity	NPC244741
0.7476	Intermediate Similarity	NPC323927

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 NPC249150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	453
0.2-0.3	584
0.3-0.4	1631
0.4-0.5	2735
0.5-0.6	2599
0.6-0.7	837
0.7-0.8	143
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4601	Approved
1.0	High Similarity	NPD4600	Approved
0.8534	High Similarity	NPD4500	Approved
0.8534	High Similarity	NPD4501	Approved
0.8158	Intermediate Similarity	NPD4499	Approved
0.8083	Intermediate Similarity	NPD4602	Approved
0.8071	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5003	Discontinued
0.795	Intermediate Similarity	NPD7957	Phase 1
0.795	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD482	Approved
0.7766	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD2095	Phase 2
0.7749	Intermediate Similarity	NPD2092	Phase 2
0.7749	Intermediate Similarity	NPD2094	Phase 2
0.7718	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2096	Phase 2
0.7708	Intermediate Similarity	NPD2091	Phase 2
0.7696	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2564	Approved
0.7692	Intermediate Similarity	NPD2565	Phase 2
0.7688	Intermediate Similarity	NPD2844	Phase 3
0.7676	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD750	Phase 2
0.7644	Intermediate Similarity	NPD5898	Approved
0.7644	Intermediate Similarity	NPD5899	Approved
0.7644	Intermediate Similarity	NPD5897	Approved
0.7606	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD4520	Approved
0.7549	Intermediate Similarity	NPD8114	Approved
0.7549	Intermediate Similarity	NPD5426	Phase 3
0.7549	Intermediate Similarity	NPD5901	Discontinued
0.7549	Intermediate Similarity	NPD8115	Approved
0.7538	Intermediate Similarity	NPD7944	Discontinued
0.7526	Intermediate Similarity	NPD6178	Phase 3
0.7522	Intermediate Similarity	NPD7955	Approved
0.7522	Intermediate Similarity	NPD7956	Approved
0.7512	Intermediate Similarity	NPD7777	Approved
0.7512	Intermediate Similarity	NPD7778	Approved
0.7512	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD4397	Phase 1
0.7512	Intermediate Similarity	NPD53	Approved
0.75	Intermediate Similarity	NPD7470	Discontinued
0.7489	Intermediate Similarity	NPD7708	Approved
0.7462	Intermediate Similarity	NPD7233	Approved
0.7462	Intermediate Similarity	NPD7234	Approved
0.7452	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2916	Discontinued
0.7419	Intermediate Similarity	NPD7730	Approved
0.7419	Intermediate Similarity	NPD7731	Approved
0.7415	Intermediate Similarity	NPD2920	Discontinued
0.7409	Intermediate Similarity	NPD7952	Approved
0.7409	Intermediate Similarity	NPD7950	Approved
0.7409	Intermediate Similarity	NPD7789	Approved
0.7409	Intermediate Similarity	NPD7953	Approved
0.7409	Intermediate Similarity	NPD7791	Approved
0.7409	Intermediate Similarity	NPD7790	Approved
0.7409	Intermediate Similarity	NPD7951	Approved
0.7407	Intermediate Similarity	NPD7271	Approved
0.7391	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6248	Phase 2
0.7389	Intermediate Similarity	NPD6249	Phase 2
0.7382	Intermediate Similarity	NPD43	Approved
0.7382	Intermediate Similarity	NPD6182	Approved
0.7382	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4334	Discontinued
0.7374	Intermediate Similarity	NPD1534	Approved
0.7371	Intermediate Similarity	NPD5473	Discontinued
0.7368	Intermediate Similarity	NPD1325	Approved
0.7368	Intermediate Similarity	NPD1326	Approved
0.7364	Intermediate Similarity	NPD4885	Approved
0.7362	Intermediate Similarity	NPD7803	Approved
0.7358	Intermediate Similarity	NPD3393	Approved
0.7358	Intermediate Similarity	NPD3394	Approved
0.7358	Intermediate Similarity	NPD3389	Approved
0.7352	Intermediate Similarity	NPD7824	Approved
0.7333	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8072	Approved
0.732	Intermediate Similarity	NPD4076	Approved
0.732	Intermediate Similarity	NPD4079	Approved
0.731	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD6664	Approved
0.7282	Intermediate Similarity	NPD6595	Phase 3
0.7277	Intermediate Similarity	NPD7618	Phase 3
0.7277	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7619	Phase 3
0.7268	Intermediate Similarity	NPD3505	Approved
0.7268	Intermediate Similarity	NPD3506	Approved
0.7268	Intermediate Similarity	NPD6479	Discontinued
0.726	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6176	Phase 1
0.7236	Intermediate Similarity	NPD8431	Approved
0.7233	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2382	Approved
0.7216	Intermediate Similarity	NPD2381	Approved
0.7216	Intermediate Similarity	NPD2380	Approved
0.7209	Intermediate Similarity	NPD7878	Phase 2
0.7208	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8073	Approved
0.7194	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2509	Approved
0.719	Intermediate Similarity	NPD2510	Approved
0.719	Intermediate Similarity	NPD7665	Phase 2
0.719	Intermediate Similarity	NPD7666	Phase 3
0.7184	Intermediate Similarity	NPD484	Approved
0.7179	Intermediate Similarity	NPD2144	Approved
0.7178	Intermediate Similarity	NPD4315	Phase 2
0.7176	Intermediate Similarity	NPD6770	Approved
0.7173	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5065	Approved
0.7157	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3038	Discontinued
0.715	Intermediate Similarity	NPD7817	Phase 1
0.715	Intermediate Similarity	NPD4948	Discontinued
0.715	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7727	Phase 2
0.7143	Intermediate Similarity	NPD8322	Phase 2
0.7143	Intermediate Similarity	NPD8386	Phase 2
0.7136	Intermediate Similarity	NPD7455	Approved
0.7136	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7454	Approved
0.7136	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5021	Discontinued
0.713	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5913	Phase 3
0.7129	Intermediate Similarity	NPD8272	Phase 2
0.7129	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5104	Approved
0.7128	Intermediate Similarity	NPD5501	Discontinued
0.7123	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6376	Discontinued
0.7104	Intermediate Similarity	NPD6165	Phase 2
0.7104	Intermediate Similarity	NPD6164	Phase 2
0.7092	Intermediate Similarity	NPD7865	Approved
0.7092	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4181	Approved
0.7089	Intermediate Similarity	NPD7070	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7482	Phase 2
0.7085	Intermediate Similarity	NPD7483	Phase 2
0.7083	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5487	Phase 1
0.7078	Intermediate Similarity	NPD6995	Phase 1
0.7078	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4506	Discontinued
0.7072	Intermediate Similarity	NPD7781	Approved
0.7072	Intermediate Similarity	NPD7780	Approved
0.7071	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3961	Discontinued
0.7056	Intermediate Similarity	NPD8358	Approved
0.7053	Intermediate Similarity	NPD6999	Discontinued
0.7053	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7716	Approved
0.7045	Intermediate Similarity	NPD7717	Approved
0.7044	Intermediate Similarity	NPD2336	Approved
0.7043	Intermediate Similarity	NPD4463	Approved
0.7043	Intermediate Similarity	NPD4462	Approved
0.7042	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6206	Phase 1
0.7037	Intermediate Similarity	NPD4326	Phase 2
0.7035	Intermediate Similarity	NPD5596	Phase 2
0.7031	Intermediate Similarity	NPD2915	Discontinued
0.703	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5444	Phase 1
0.7009	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6641	Approved
0.7005	Intermediate Similarity	NPD7946	Pre-registration
0.7005	Intermediate Similarity	NPD6261	Phase 3
0.7005	Intermediate Similarity	NPD2882	Phase 1
0.7005	Intermediate Similarity	NPD6642	Approved
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5835	Phase 3
0.6995	Remote Similarity	NPD5834	Phase 3
0.6991	Remote Similarity	NPD7707	Approved
0.6983	Remote Similarity	NPD8364	Approved
0.6983	Remote Similarity	NPD8363	Approved
0.6979	Remote Similarity	NPD3323	Discontinued
0.6978	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8093	Discontinued
0.6973	Remote Similarity	NPD1683	Approved
0.6967	Remote Similarity	NPD6987	Phase 1
0.6967	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5592	Clinical (unspecified phase)

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