NPASS Compound

Structure

NPC230849 OpenBabel07101718312D 28 32 0 0 1 0 0 0 0 0999 V2000 8.9477 1.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 -2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 -1.8666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6160 1.5965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 1.5069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5328 -1.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5369 -1.6051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3070 0.8737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2938 0.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2898 0.2772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 -0.8666 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9259 -0.7752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3143 -0.6301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0691 0.6723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9008 -0.5527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3781 -0.2788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5123 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1728 -0.1172 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 9.4318 -1.0907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0691 0.6723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6539 -1.2106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 12 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 1 1 6 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 3 1 6 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 6 0 0 0 15 19 1 0 0 0 0 15 23 1 1 0 0 0 16 5 1 6 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 9 1 6 0 0 0 17 27 1 0 0 0 0 18 10 1 1 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 20 26 1 0 0 0 0 21 24 2 0 0 0 0 21 27 1 0 0 0 0 22 25 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	389.22
Volume:	393.324
LogP:	3.962
LogD:	3.503
LogS:	-3.523
# Rotatable Bonds:	2
TPSA:	72.14
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	5.071
Fsp3:	0.773
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:	-4.844
MDCK Permeability:	5.863256228622049e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.111
Human Intestinal Absorption (HIA):	0.19
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.722

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	77.01213836669922%
Volume Distribution (VD):	3.613
Pgp-substrate:	20.075471878051758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.188
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.654
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.777

ADMET: Excretion

Clearance (CL):	13.464
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.506
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.414
Skin Sensitization:	0.54
Carcinogencity:	0.464
Eye Corrosion:	0.006
Eye Irritation:	0.012
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC230849

Natural Product ID:	NPC230849
*Common Name:**	QAAYWVNRGVTWRB-PMVIMNEFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QAAYWVNRGVTWRB-PMVIMNEFSA-N
Standard InCHI:	InChI=1S/C22H31NO5/c1-11-9-17(27-21(11)24)14-6-7-15-19-13(3)20(18-10-12(2)22(25)28-18)26-16(19)5-4-8-23(14)15/h10-11,13-20H,4-9H2,1-3H3/t11-,13-,14-,15-,16+,17-,18+,19+,20-/m0/s1
SMILES:	C[C@H]1[C@H]2[C@H](O[C@@H]1[C@H]1C=C(C(=O)O1)C)CCCN1[C@H]2CC[C@H]1[C@@H]1C[C@@H](C(=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256145
PubChem CID:	24769901
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003427] Stemona alkaloids [CHEMONTID:0003914] Stemoamide-type 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
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	stems and leaves	n.a.	n.a.	PMID[18163592]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28230	Stemona japonica	Species	Stemonaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4586	Individual Protein	Nicotinic acetylcholine receptor alpha1 subunit	Heliothis virescens	Activity	=	90.0	%	PMID[492561]

☑ 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 NPC230849 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	148
0.1-0.2	1012
0.2-0.3	6681
0.3-0.4	21361
0.4-0.5	10635
0.5-0.6	2483
0.6-0.7	315
0.7-0.8	57
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9123	High Similarity	NPC174463
0.8607	High Similarity	NPC173173
0.8333	Intermediate Similarity	NPC11379
0.792	Intermediate Similarity	NPC469999
0.7891	Intermediate Similarity	NPC215507
0.7815	Intermediate Similarity	NPC58281
0.7752	Intermediate Similarity	NPC307165
0.7717	Intermediate Similarity	NPC329401
0.7717	Intermediate Similarity	NPC477987
0.7634	Intermediate Similarity	NPC133089
0.7627	Intermediate Similarity	NPC271562
0.7603	Intermediate Similarity	NPC43648
0.7581	Intermediate Similarity	NPC235625
0.752	Intermediate Similarity	NPC138534
0.752	Intermediate Similarity	NPC477986
0.75	Intermediate Similarity	NPC471087
0.75	Intermediate Similarity	NPC477985
0.75	Intermediate Similarity	NPC326386
0.7481	Intermediate Similarity	NPC477988
0.7456	Intermediate Similarity	NPC471843
0.7398	Intermediate Similarity	NPC130124
0.7398	Intermediate Similarity	NPC193471
0.736	Intermediate Similarity	NPC65045
0.736	Intermediate Similarity	NPC469997
0.7328	Intermediate Similarity	NPC471086
0.7287	Intermediate Similarity	NPC323168
0.7287	Intermediate Similarity	NPC111162
0.7287	Intermediate Similarity	NPC477989
0.7287	Intermediate Similarity	NPC293550
0.7287	Intermediate Similarity	NPC477990
0.725	Intermediate Similarity	NPC471844
0.7165	Intermediate Similarity	NPC201889
0.7165	Intermediate Similarity	NPC106791
0.7165	Intermediate Similarity	NPC284656
0.7132	Intermediate Similarity	NPC23963
0.7132	Intermediate Similarity	NPC470000
0.7097	Intermediate Similarity	NPC181510
0.7097	Intermediate Similarity	NPC47857
0.7097	Intermediate Similarity	NPC168758
0.7083	Intermediate Similarity	NPC265094
0.7069	Intermediate Similarity	NPC150041
0.6967	Remote Similarity	NPC93179
0.696	Remote Similarity	NPC30911
0.696	Remote Similarity	NPC316984
0.6949	Remote Similarity	NPC476344
0.6917	Remote Similarity	NPC474371
0.6912	Remote Similarity	NPC120335
0.6889	Remote Similarity	NPC470539
0.6885	Remote Similarity	NPC44514
0.6866	Remote Similarity	NPC476951
0.6791	Remote Similarity	NPC309525
0.6772	Remote Similarity	NPC469466
0.6721	Remote Similarity	NPC287638
0.6721	Remote Similarity	NPC194750
0.6721	Remote Similarity	NPC233274
0.6667	Remote Similarity	NPC88190
0.6641	Remote Similarity	NPC476952
0.6636	Remote Similarity	NPC216090
0.6615	Remote Similarity	NPC471846
0.6615	Remote Similarity	NPC39041
0.6615	Remote Similarity	NPC241294
0.6615	Remote Similarity	NPC202722
0.6615	Remote Similarity	NPC471845
0.6613	Remote Similarity	NPC64168
0.6532	Remote Similarity	NPC6271
0.6532	Remote Similarity	NPC279833
0.6532	Remote Similarity	NPC80439
0.6532	Remote Similarity	NPC173690
0.6522	Remote Similarity	NPC469861
0.6522	Remote Similarity	NPC284902
0.6522	Remote Similarity	NPC469860
0.6522	Remote Similarity	NPC130436
0.6466	Remote Similarity	NPC475703
0.6452	Remote Similarity	NPC86077
0.6435	Remote Similarity	NPC215364
0.6417	Remote Similarity	NPC473316
0.6417	Remote Similarity	NPC473330
0.6404	Remote Similarity	NPC318468
0.6404	Remote Similarity	NPC475947
0.6391	Remote Similarity	NPC156336
0.6391	Remote Similarity	NPC200412
0.6391	Remote Similarity	NPC120599
0.6385	Remote Similarity	NPC276995
0.6385	Remote Similarity	NPC76660
0.6379	Remote Similarity	NPC64153
0.6371	Remote Similarity	NPC188785
0.6364	Remote Similarity	NPC123360
0.6364	Remote Similarity	NPC224689
0.6356	Remote Similarity	NPC295312
0.6333	Remote Similarity	NPC469998
0.6333	Remote Similarity	NPC179746
0.6333	Remote Similarity	NPC475657
0.6333	Remote Similarity	NPC81419
0.6328	Remote Similarity	NPC474099
0.6325	Remote Similarity	NPC160138
0.6325	Remote Similarity	NPC231889
0.632	Remote Similarity	NPC473289
0.6319	Remote Similarity	NPC45813
0.6316	Remote Similarity	NPC173609
0.6303	Remote Similarity	NPC80875
0.6293	Remote Similarity	NPC235792
0.6281	Remote Similarity	NPC477131
0.6277	Remote Similarity	NPC318445
0.6277	Remote Similarity	NPC316133
0.6271	Remote Similarity	NPC242364
0.6271	Remote Similarity	NPC320569
0.6271	Remote Similarity	NPC133730
0.6271	Remote Similarity	NPC274446
0.6271	Remote Similarity	NPC172821
0.6271	Remote Similarity	NPC39754
0.6271	Remote Similarity	NPC171135
0.6271	Remote Similarity	NPC169511
0.6271	Remote Similarity	NPC61257
0.6271	Remote Similarity	NPC100454
0.6271	Remote Similarity	NPC81045
0.6271	Remote Similarity	NPC234077
0.6271	Remote Similarity	NPC287164
0.6271	Remote Similarity	NPC191929
0.6271	Remote Similarity	NPC261952
0.6271	Remote Similarity	NPC151403
0.627	Remote Similarity	NPC199831
0.627	Remote Similarity	NPC474827
0.627	Remote Similarity	NPC68001
0.627	Remote Similarity	NPC215988
0.627	Remote Similarity	NPC474828
0.6269	Remote Similarity	NPC9714
0.6261	Remote Similarity	NPC170286
0.626	Remote Similarity	NPC261750
0.626	Remote Similarity	NPC60432
0.626	Remote Similarity	NPC1111
0.625	Remote Similarity	NPC128276
0.625	Remote Similarity	NPC110875
0.625	Remote Similarity	NPC72183
0.625	Remote Similarity	NPC208886
0.625	Remote Similarity	NPC82129
0.625	Remote Similarity	NPC299808
0.625	Remote Similarity	NPC12172
0.625	Remote Similarity	NPC118844
0.6241	Remote Similarity	NPC30196
0.6241	Remote Similarity	NPC470538
0.6239	Remote Similarity	NPC107787
0.6231	Remote Similarity	NPC196073
0.6231	Remote Similarity	NPC469603
0.6231	Remote Similarity	NPC195435
0.623	Remote Similarity	NPC304886
0.6228	Remote Similarity	NPC471325
0.6222	Remote Similarity	NPC471261
0.622	Remote Similarity	NPC75523
0.622	Remote Similarity	NPC133420
0.6218	Remote Similarity	NPC42598
0.6218	Remote Similarity	NPC81778
0.6218	Remote Similarity	NPC93794
0.6218	Remote Similarity	NPC474032
0.6218	Remote Similarity	NPC91067
0.6218	Remote Similarity	NPC473504
0.6218	Remote Similarity	NPC40066
0.6218	Remote Similarity	NPC318963
0.6218	Remote Similarity	NPC20621
0.6214	Remote Similarity	NPC478136
0.621	Remote Similarity	NPC208233
0.621	Remote Similarity	NPC187268
0.6202	Remote Similarity	NPC470535
0.6202	Remote Similarity	NPC70235
0.6197	Remote Similarity	NPC316401
0.6197	Remote Similarity	NPC189393
0.6197	Remote Similarity	NPC90814
0.6195	Remote Similarity	NPC178277
0.6194	Remote Similarity	NPC6531
0.6194	Remote Similarity	NPC147707
0.6182	Remote Similarity	NPC476355
0.6181	Remote Similarity	NPC239252
0.6181	Remote Similarity	NPC473703
0.6181	Remote Similarity	NPC471256
0.617	Remote Similarity	NPC97861
0.6167	Remote Similarity	NPC312042
0.6167	Remote Similarity	NPC51004
0.6167	Remote Similarity	NPC159568
0.6167	Remote Similarity	NPC239517
0.6167	Remote Similarity	NPC62815
0.6167	Remote Similarity	NPC475748
0.6165	Remote Similarity	NPC474984
0.6161	Remote Similarity	NPC470240
0.6161	Remote Similarity	NPC476794
0.6161	Remote Similarity	NPC57744
0.616	Remote Similarity	NPC469402
0.6154	Remote Similarity	NPC319036
0.6154	Remote Similarity	NPC77871
0.6154	Remote Similarity	NPC9678
0.6154	Remote Similarity	NPC473156
0.6154	Remote Similarity	NPC39279
0.6154	Remote Similarity	NPC78089
0.6154	Remote Similarity	NPC475268
0.6154	Remote Similarity	NPC235809
0.6154	Remote Similarity	NPC202055
0.6154	Remote Similarity	NPC99395
0.6154	Remote Similarity	NPC470536
0.6154	Remote Similarity	NPC39167
0.6154	Remote Similarity	NPC473671
0.6154	Remote Similarity	NPC197903
0.6154	Remote Similarity	NPC25764

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 NPC230849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	117
0.1-0.2	832
0.2-0.3	3424
0.3-0.4	3710
0.4-0.5	928
0.5-0.6	134
0.6-0.7	5
0.7-0.8	0
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
0.696	Remote Similarity	NPD2204	Approved
0.6277	Remote Similarity	NPD7642	Approved
0.6269	Remote Similarity	NPD7641	Discontinued
0.6142	Remote Similarity	NPD2259	Approved
0.6142	Remote Similarity	NPD2258	Approved
0.6103	Remote Similarity	NPD2132	Phase 3
0.6099	Remote Similarity	NPD8336	Approved
0.6099	Remote Similarity	NPD8337	Approved
0.6084	Remote Similarity	NPD2101	Approved
0.6081	Remote Similarity	NPD2569	Approved
0.6081	Remote Similarity	NPD2567	Approved
0.6071	Remote Similarity	NPD8451	Approved
0.6048	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6845	Suspended
0.6028	Remote Similarity	NPD8448	Approved
0.6017	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD8392	Approved
0.6014	Remote Similarity	NPD8390	Approved
0.6014	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.597	Remote Similarity	NPD1376	Discontinued
0.5957	Remote Similarity	NPD8273	Phase 1
0.595	Remote Similarity	NPD1695	Approved
0.5931	Remote Similarity	NPD8338	Approved
0.5899	Remote Similarity	NPD8269	Approved
0.5899	Remote Similarity	NPD8266	Approved
0.5899	Remote Similarity	NPD8268	Approved
0.5899	Remote Similarity	NPD8267	Approved
0.5887	Remote Similarity	NPD8299	Approved
0.5887	Remote Similarity	NPD8341	Approved
0.5887	Remote Similarity	NPD8342	Approved
0.5887	Remote Similarity	NPD8340	Approved
0.5865	Remote Similarity	NPD6421	Discontinued
0.5839	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD1689	Approved
0.5811	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4211	Phase 1
0.5772	Remote Similarity	NPD6698	Approved
0.5772	Remote Similarity	NPD46	Approved
0.5753	Remote Similarity	NPD7260	Phase 2
0.5745	Remote Similarity	NPD8080	Discontinued
0.5743	Remote Similarity	NPD8415	Approved
0.5714	Remote Similarity	NPD2613	Approved
0.5705	Remote Similarity	NPD3614	Approved
0.5705	Remote Similarity	NPD3089	Approved
0.5705	Remote Similarity	NPD3616	Approved
0.5705	Remote Similarity	NPD2574	Discontinued
0.5705	Remote Similarity	NPD4745	Approved
0.5705	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD4746	Phase 3
0.5705	Remote Similarity	NPD2566	Approved
0.5705	Remote Similarity	NPD3087	Approved
0.5705	Remote Similarity	NPD3615	Approved
0.5705	Remote Similarity	NPD2570	Approved
0.5705	Remote Similarity	NPD3088	Approved
0.5705	Remote Similarity	NPD2571	Approved
0.5705	Remote Similarity	NPD2573	Approved
0.5705	Remote Similarity	NPD3090	Approved
0.5704	Remote Similarity	NPD7829	Approved
0.5704	Remote Similarity	NPD7830	Approved
0.568	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD3664	Approved
0.5646	Remote Similarity	NPD3662	Phase 3
0.5646	Remote Similarity	NPD3661	Approved
0.5646	Remote Similarity	NPD3663	Approved
0.5641	Remote Similarity	NPD2575	Approved
0.5638	Remote Similarity	NPD4619	Approved
0.5638	Remote Similarity	NPD4621	Approved
0.563	Remote Similarity	NPD6420	Discontinued
0.563	Remote Similarity	NPD6371	Approved
0.563	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD4686	Approved
0.5629	Remote Similarity	NPD4685	Phase 3
0.5629	Remote Similarity	NPD4684	Phase 3
0.5621	Remote Similarity	NPD6077	Discontinued

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