NPASS Compound

Structure

NPC41551 OpenBabel07101719132D 25 28 0 0 1 0 0 0 0 0999 V2000 5.4263 -1.9377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4438 0.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 1.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9499 -1.8198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9204 -2.7563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9586 -2.7275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0104 0.5965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0104 -0.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4175 0.8669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6105 0.2501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6105 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5896 0.2501 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5027 -1.8802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5024 -0.1371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0849 -1.0040 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8069 0.5279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5896 -0.4428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1314 -0.8749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9595 0.0719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4438 -0.9240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0085 -1.0616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4492 0.0347 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 1.1314 0.6821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5409 -1.8514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 10 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 11 20 2 0 0 0 0 12 17 1 1 0 0 0 12 24 1 0 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 6 0 0 0 15 18 1 1 0 0 0 15 25 1 0 0 0 0 16 19 1 1 0 0 0 16 24 1 0 0 0 0 17 18 1 1 0 0 0 18 19 1 1 0 0 0 19 9 1 6 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	345.15
LogP:	1.764
LogD:	0.961
LogS:	-3.903
# Rotatable Bonds:	3
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	6.354
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.923
MDCK Permeability:	1.4206740161171183e-05
Pgp-inhibitor:	0.93
Pgp-substrate:	0.623
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.762
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	73.55795288085938%
Volume Distribution (VD):	0.89
Pgp-substrate:	29.24778175354004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.645
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.598

ADMET: Excretion

Clearance (CL):	8.69
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.56
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.59
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.592
Carcinogencity:	0.853
Eye Corrosion:	0.308
Eye Irritation:	0.085
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC41551

Natural Product ID:	NPC41551
*Common Name:**	Trichothecinol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RVOJMELIZZNGBE-DUGZWPNFSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-5-6-13(21)25-15-14(22)16-19(9-23-19)18(15,4)17(3)8-11(20)10(2)7-12(17)24-16/h5-7,12,14-16,22H,8-9H2,1-4H3/b6-5-/t12-,14-,15-,16-,17+,18-,19+/m1/s1
SMILES:	C/C=CC(=O)O[C@@H]1[C@H]([C@@H]2[C@@]3(CO3)[C@@]1(C)[C@@]1(C)CC(=O)C(=C[C@H]1O2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519098
PubChem CID:	10472929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650079]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441070]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12483	Holarrhena floribunda	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
EC50	4
Others	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.014	ug.mL-1	PMID[568440]
NPT2359	Cell Line	SK-MEL-30	Homo sapiens	EC50	=	0.013	ug.mL-1	PMID[568440]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	0.021	ug.mL-1	PMID[568440]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	0.014	ug.mL-1	PMID[568440]
NPT140	Organism	Artemia	Artemia	LC50	=	0.52	ug.mL-1	PMID[568440]

☑ 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 NPC41551 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	204
0.1-0.2	1238
0.2-0.3	4387
0.3-0.4	8172
0.4-0.5	13496
0.5-0.6	7556
0.6-0.7	5756
0.7-0.8	1726
0.8-0.85	107
0.85-0.9	45
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC50223
0.9505	High Similarity	NPC169843
0.9406	High Similarity	NPC123505
0.9143	High Similarity	NPC77089
0.9109	High Similarity	NPC79631
0.8899	High Similarity	NPC305044
0.8899	High Similarity	NPC265290
0.8889	High Similarity	NPC313921
0.8889	High Similarity	NPC98038
0.8846	High Similarity	NPC260809
0.8846	High Similarity	NPC474783
0.8807	High Similarity	NPC101400
0.8807	High Similarity	NPC101965
0.8796	High Similarity	NPC474750
0.875	High Similarity	NPC252242
0.875	High Similarity	NPC475956
0.8713	High Similarity	NPC240838
0.8679	High Similarity	NPC469960
0.8679	High Similarity	NPC29389
0.8679	High Similarity	NPC93026
0.8679	High Similarity	NPC265502
0.8661	High Similarity	NPC474286
0.8661	High Similarity	NPC475130
0.8654	High Similarity	NPC26557
0.8641	High Similarity	NPC79449
0.8641	High Similarity	NPC474957
0.8611	High Similarity	NPC187876
0.8598	High Similarity	NPC472263
0.8598	High Similarity	NPC469957
0.8598	High Similarity	NPC108682
0.8598	High Similarity	NPC469959
0.8571	High Similarity	NPC475986
0.8571	High Similarity	NPC200672
0.8571	High Similarity	NPC214714
0.8544	High Similarity	NPC476057
0.8544	High Similarity	NPC182811
0.8544	High Similarity	NPC347923
0.8519	High Similarity	NPC10150
0.8509	High Similarity	NPC79579
0.8491	Intermediate Similarity	NPC232515
0.8462	Intermediate Similarity	NPC274458
0.8333	Intermediate Similarity	NPC475401
0.8333	Intermediate Similarity	NPC54737
0.8333	Intermediate Similarity	NPC153440
0.8286	Intermediate Similarity	NPC65700
0.8261	Intermediate Similarity	NPC5292
0.8261	Intermediate Similarity	NPC477092
0.8246	Intermediate Similarity	NPC475305
0.8214	Intermediate Similarity	NPC126691
0.8208	Intermediate Similarity	NPC13743
0.8208	Intermediate Similarity	NPC98813
0.8205	Intermediate Similarity	NPC107493
0.8198	Intermediate Similarity	NPC5103
0.819	Intermediate Similarity	NPC474585
0.8182	Intermediate Similarity	NPC472825
0.8158	Intermediate Similarity	NPC190286
0.8142	Intermediate Similarity	NPC287075
0.8136	Intermediate Similarity	NPC469789
0.812	Intermediate Similarity	NPC46570
0.812	Intermediate Similarity	NPC310511
0.8113	Intermediate Similarity	NPC222303
0.8108	Intermediate Similarity	NPC139838
0.8108	Intermediate Similarity	NPC59489
0.8103	Intermediate Similarity	NPC305260
0.8103	Intermediate Similarity	NPC270850
0.8083	Intermediate Similarity	NPC287423
0.8067	Intermediate Similarity	NPC81736
0.8067	Intermediate Similarity	NPC172154
0.8053	Intermediate Similarity	NPC236217
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC293112
0.8	Intermediate Similarity	NPC270013
0.7983	Intermediate Similarity	NPC11895
0.7982	Intermediate Similarity	NPC474775
0.7982	Intermediate Similarity	NPC469454
0.7982	Intermediate Similarity	NPC317210
0.7982	Intermediate Similarity	NPC110989
0.7982	Intermediate Similarity	NPC469463
0.7982	Intermediate Similarity	NPC469496
0.7981	Intermediate Similarity	NPC212486
0.7966	Intermediate Similarity	NPC472000
0.7966	Intermediate Similarity	NPC471999
0.7966	Intermediate Similarity	NPC472001
0.7966	Intermediate Similarity	NPC67569
0.7965	Intermediate Similarity	NPC71680
0.7965	Intermediate Similarity	NPC304180
0.7965	Intermediate Similarity	NPC475495
0.7965	Intermediate Similarity	NPC179798
0.7963	Intermediate Similarity	NPC150923
0.7961	Intermediate Similarity	NPC197107
0.7951	Intermediate Similarity	NPC470880
0.7949	Intermediate Similarity	NPC475041
0.7949	Intermediate Similarity	NPC472667
0.7949	Intermediate Similarity	NPC61520
0.7949	Intermediate Similarity	NPC473203
0.7944	Intermediate Similarity	NPC212465
0.7944	Intermediate Similarity	NPC177232
0.7944	Intermediate Similarity	NPC83895
0.7944	Intermediate Similarity	NPC187761
0.7934	Intermediate Similarity	NPC473253
0.7928	Intermediate Similarity	NPC470192
0.7917	Intermediate Similarity	NPC8369
0.7917	Intermediate Similarity	NPC8374
0.7913	Intermediate Similarity	NPC471398
0.7913	Intermediate Similarity	NPC474181
0.7913	Intermediate Similarity	NPC178289
0.7909	Intermediate Similarity	NPC203659
0.7909	Intermediate Similarity	NPC474741
0.7905	Intermediate Similarity	NPC474035
0.7905	Intermediate Similarity	NPC81386
0.7899	Intermediate Similarity	NPC470265
0.7899	Intermediate Similarity	NPC23786
0.7899	Intermediate Similarity	NPC170538
0.7895	Intermediate Similarity	NPC477093
0.7895	Intermediate Similarity	NPC473522
0.7895	Intermediate Similarity	NPC475277
0.789	Intermediate Similarity	NPC225353
0.7886	Intermediate Similarity	NPC213634
0.7881	Intermediate Similarity	NPC474370
0.7881	Intermediate Similarity	NPC143755
0.7876	Intermediate Similarity	NPC206595
0.7876	Intermediate Similarity	NPC193741
0.7876	Intermediate Similarity	NPC37116
0.7876	Intermediate Similarity	NPC15551
0.787	Intermediate Similarity	NPC475053
0.787	Intermediate Similarity	NPC186861
0.787	Intermediate Similarity	NPC471381
0.787	Intermediate Similarity	NPC280963
0.7863	Intermediate Similarity	NPC329736
0.7863	Intermediate Similarity	NPC13710
0.7851	Intermediate Similarity	NPC159499
0.7851	Intermediate Similarity	NPC473635
0.785	Intermediate Similarity	NPC70145
0.785	Intermediate Similarity	NPC471150
0.785	Intermediate Similarity	NPC91695
0.785	Intermediate Similarity	NPC40812
0.7845	Intermediate Similarity	NPC298278
0.7845	Intermediate Similarity	NPC106228
0.7845	Intermediate Similarity	NPC138372
0.7845	Intermediate Similarity	NPC148458
0.7845	Intermediate Similarity	NPC176840
0.784	Intermediate Similarity	NPC471234
0.7838	Intermediate Similarity	NPC96377
0.7838	Intermediate Similarity	NPC223450
0.7833	Intermediate Similarity	NPC473979
0.7833	Intermediate Similarity	NPC204812
0.783	Intermediate Similarity	NPC214694
0.7826	Intermediate Similarity	NPC250109
0.7826	Intermediate Similarity	NPC56448
0.7826	Intermediate Similarity	NPC962
0.7826	Intermediate Similarity	NPC194100
0.7823	Intermediate Similarity	NPC471855
0.7818	Intermediate Similarity	NPC472747
0.7818	Intermediate Similarity	NPC472750
0.7818	Intermediate Similarity	NPC475945
0.7818	Intermediate Similarity	NPC473624
0.7818	Intermediate Similarity	NPC475871
0.7815	Intermediate Similarity	NPC473228
0.7815	Intermediate Similarity	NPC470829
0.781	Intermediate Similarity	NPC475912
0.7807	Intermediate Similarity	NPC317107
0.7805	Intermediate Similarity	NPC231529
0.7798	Intermediate Similarity	NPC471401
0.7798	Intermediate Similarity	NPC171759
0.7798	Intermediate Similarity	NPC476270
0.7798	Intermediate Similarity	NPC477950
0.7797	Intermediate Similarity	NPC476960
0.7797	Intermediate Similarity	NPC264954
0.7787	Intermediate Similarity	NPC473265
0.7778	Intermediate Similarity	NPC470492
0.7778	Intermediate Similarity	NPC261377
0.7778	Intermediate Similarity	NPC255592
0.7778	Intermediate Similarity	NPC473326
0.7778	Intermediate Similarity	NPC308567
0.7778	Intermediate Similarity	NPC469684
0.7778	Intermediate Similarity	NPC239273
0.7769	Intermediate Similarity	NPC241456
0.7769	Intermediate Similarity	NPC32868
0.7759	Intermediate Similarity	NPC473898
0.7759	Intermediate Similarity	NPC238667
0.7759	Intermediate Similarity	NPC326542
0.7757	Intermediate Similarity	NPC18019
0.7757	Intermediate Similarity	NPC24956
0.7757	Intermediate Similarity	NPC476315
0.775	Intermediate Similarity	NPC88326
0.775	Intermediate Similarity	NPC269642
0.775	Intermediate Similarity	NPC153700
0.7748	Intermediate Similarity	NPC146731
0.7748	Intermediate Similarity	NPC472748
0.7748	Intermediate Similarity	NPC100487
0.7748	Intermediate Similarity	NPC296950
0.7748	Intermediate Similarity	NPC470104
0.7748	Intermediate Similarity	NPC255309
0.7748	Intermediate Similarity	NPC309190
0.7748	Intermediate Similarity	NPC258532
0.7739	Intermediate Similarity	NPC475851
0.7739	Intermediate Similarity	NPC221144
0.7739	Intermediate Similarity	NPC317687
0.7739	Intermediate Similarity	NPC475524

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 NPC41551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1525
0.2-0.3	3804
0.3-0.4	2428
0.4-0.5	718
0.5-0.6	254
0.6-0.7	197
0.7-0.8	50
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
0.7731	Intermediate Similarity	NPD6319	Approved
0.7719	Intermediate Similarity	NPD6371	Approved
0.7672	Intermediate Similarity	NPD4632	Approved
0.7627	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD6698	Approved
0.7619	Intermediate Similarity	NPD46	Approved
0.7586	Intermediate Similarity	NPD6053	Discontinued
0.7456	Intermediate Similarity	NPD5697	Approved
0.7456	Intermediate Similarity	NPD6412	Phase 2
0.7436	Intermediate Similarity	NPD8297	Approved
0.7419	Intermediate Similarity	NPD7507	Approved
0.7391	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD6881	Approved
0.7368	Intermediate Similarity	NPD6008	Approved
0.735	Intermediate Similarity	NPD6649	Approved
0.735	Intermediate Similarity	NPD6650	Approved
0.7339	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD6009	Approved
0.7328	Intermediate Similarity	NPD6014	Approved
0.7328	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6013	Approved
0.7328	Intermediate Similarity	NPD6012	Approved
0.7304	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6054	Approved
0.729	Intermediate Similarity	NPD5785	Approved
0.728	Intermediate Similarity	NPD6616	Approved
0.7265	Intermediate Similarity	NPD7290	Approved
0.7265	Intermediate Similarity	NPD7102	Approved
0.7265	Intermediate Similarity	NPD4634	Approved
0.7265	Intermediate Similarity	NPD6883	Approved
0.7258	Intermediate Similarity	NPD7604	Phase 2
0.7244	Intermediate Similarity	NPD7319	Approved
0.7241	Intermediate Similarity	NPD6011	Approved
0.7236	Intermediate Similarity	NPD5983	Phase 2
0.7236	Intermediate Similarity	NPD6016	Approved
0.7236	Intermediate Similarity	NPD6015	Approved
0.7222	Intermediate Similarity	NPD7078	Approved
0.7217	Intermediate Similarity	NPD5739	Approved
0.7217	Intermediate Similarity	NPD6675	Approved
0.7217	Intermediate Similarity	NPD7128	Approved
0.7217	Intermediate Similarity	NPD6402	Approved
0.7203	Intermediate Similarity	NPD6617	Approved
0.7203	Intermediate Similarity	NPD8130	Phase 1
0.7203	Intermediate Similarity	NPD6847	Approved
0.7203	Intermediate Similarity	NPD6869	Approved
0.7184	Intermediate Similarity	NPD6435	Approved
0.7182	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6373	Approved
0.7179	Intermediate Similarity	NPD6372	Approved
0.7177	Intermediate Similarity	NPD6370	Approved
0.7177	Intermediate Similarity	NPD5988	Approved
0.7165	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.713	Intermediate Similarity	NPD7838	Discovery
0.7119	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5211	Phase 2
0.7097	Intermediate Similarity	NPD7503	Approved
0.7094	Intermediate Similarity	NPD7320	Approved
0.708	Intermediate Similarity	NPD4696	Approved
0.708	Intermediate Similarity	NPD5286	Approved
0.708	Intermediate Similarity	NPD7640	Approved
0.708	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD5285	Approved
0.7054	Intermediate Similarity	NPD6083	Phase 2
0.7054	Intermediate Similarity	NPD6084	Phase 2
0.7027	Intermediate Similarity	NPD5695	Phase 3
0.7016	Intermediate Similarity	NPD6059	Approved
0.7008	Intermediate Similarity	NPD6336	Discontinued
0.7	Intermediate Similarity	NPD7260	Phase 2
0.6991	Remote Similarity	NPD5696	Approved
0.699	Remote Similarity	NPD5368	Approved
0.6983	Remote Similarity	NPD5141	Approved
0.6981	Remote Similarity	NPD1694	Approved
0.6981	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5224	Approved
0.6957	Remote Similarity	NPD5225	Approved
0.6957	Remote Similarity	NPD5226	Approved
0.6957	Remote Similarity	NPD4633	Approved
0.6953	Remote Similarity	NPD8293	Discontinued
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5284	Approved
0.6909	Remote Similarity	NPD5281	Approved
0.6903	Remote Similarity	NPD4755	Approved
0.6897	Remote Similarity	NPD5175	Approved
0.6897	Remote Similarity	NPD5174	Approved
0.6881	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4629	Approved
0.687	Remote Similarity	NPD5223	Approved
0.687	Remote Similarity	NPD5344	Discontinued
0.6864	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7327	Approved
0.6855	Remote Similarity	NPD7328	Approved
0.6842	Remote Similarity	NPD4225	Approved
0.6842	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6274	Approved
0.6825	Remote Similarity	NPD8517	Approved
0.6825	Remote Similarity	NPD8516	Approved
0.6825	Remote Similarity	NPD8513	Phase 3
0.6825	Remote Similarity	NPD8033	Approved
0.6825	Remote Similarity	NPD8515	Approved
0.6822	Remote Similarity	NPD5363	Approved
0.68	Remote Similarity	NPD7100	Approved
0.68	Remote Similarity	NPD7101	Approved
0.68	Remote Similarity	NPD7516	Approved
0.6786	Remote Similarity	NPD5282	Discontinued
0.6783	Remote Similarity	NPD4700	Approved
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6317	Approved
0.6759	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD6409	Approved
0.6759	Remote Similarity	NPD7334	Approved
0.6759	Remote Similarity	NPD5786	Approved
0.6759	Remote Similarity	NPD4249	Approved
0.6759	Remote Similarity	NPD6684	Approved
0.6759	Remote Similarity	NPD5330	Approved
0.6759	Remote Similarity	NPD7146	Approved
0.6757	Remote Similarity	NPD5693	Phase 1
0.6757	Remote Similarity	NPD7983	Approved
0.6746	Remote Similarity	NPD8294	Approved
0.6746	Remote Similarity	NPD8377	Approved
0.6729	Remote Similarity	NPD3665	Phase 1
0.6729	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD3666	Approved
0.6727	Remote Similarity	NPD4753	Phase 2
0.672	Remote Similarity	NPD6314	Approved
0.672	Remote Similarity	NPD6335	Approved
0.672	Remote Similarity	NPD6313	Approved
0.6697	Remote Similarity	NPD4251	Approved
0.6697	Remote Similarity	NPD4250	Approved
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD6399	Phase 3
0.6693	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8380	Approved
0.6693	Remote Similarity	NPD8379	Approved
0.6693	Remote Similarity	NPD8296	Approved
0.6693	Remote Similarity	NPD8335	Approved
0.6693	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6903	Approved
0.6607	Remote Similarity	NPD6411	Approved
0.6607	Remote Similarity	NPD6079	Approved
0.6604	Remote Similarity	NPD5369	Approved
0.6589	Remote Similarity	NPD8328	Phase 3
0.6589	Remote Similarity	NPD7642	Approved
0.6579	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6845	Suspended
0.6565	Remote Similarity	NPD8074	Phase 3
0.6557	Remote Similarity	NPD5248	Approved
0.6557	Remote Similarity	NPD5251	Approved
0.6557	Remote Similarity	NPD5250	Approved
0.6557	Remote Similarity	NPD5247	Approved
0.6557	Remote Similarity	NPD5249	Phase 3
0.6549	Remote Similarity	NPD4202	Approved
0.6542	Remote Similarity	NPD4270	Approved
0.6542	Remote Similarity	NPD4269	Approved
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5956	Approved
0.6535	Remote Similarity	NPD4522	Approved
0.6532	Remote Similarity	NPD8133	Approved
0.6529	Remote Similarity	NPD5128	Approved
0.6525	Remote Similarity	NPD7632	Discontinued
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5207	Approved
0.6515	Remote Similarity	NPD6033	Approved
0.6514	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5217	Approved
0.6504	Remote Similarity	NPD5216	Approved
0.6504	Remote Similarity	NPD5215	Approved
0.65	Remote Similarity	NPD4768	Approved
0.65	Remote Similarity	NPD4767	Approved
0.6496	Remote Similarity	NPD6648	Approved
0.6481	Remote Similarity	NPD7154	Phase 3
0.6481	Remote Similarity	NPD5362	Discontinued
0.6476	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4271	Approved
0.6476	Remote Similarity	NPD4268	Approved
0.6471	Remote Similarity	NPD4754	Approved
0.6466	Remote Similarity	NPD5173	Approved
0.6462	Remote Similarity	NPD7830	Approved
0.6462	Remote Similarity	NPD7829	Approved
0.646	Remote Similarity	NPD5694	Approved
0.6455	Remote Similarity	NPD5690	Phase 2
0.6455	Remote Similarity	NPD3618	Phase 1
0.6434	Remote Similarity	NPD6909	Approved
0.6434	Remote Similarity	NPD6908	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